DIY vs Delegate

I am a bad delegator and very much a do it yourselfer (DIY). It’s one of the many reasons I am certain I’d make a terrible CEO.

CEOs must delegate. At scale, they should only do three things; set the vision and strategy and continuously communicate it, recruit and retain the very best people, and keep the company funded. Everything else has to be delegated at scale.

But when you start a company, you (and your cofounders) have to do everything yourself. There is nobody to delegate things to. And hiring a bunch of people to do things like schedule your meetings, answer the phones, keep the books, review contracts, interview candidates, etc is a bad idea because it uses up money which is always in short supply at the early stage of a startup. You can, and should, see if there are service providers who are inexpensive who can help. Bookkeeping is one area where that is certainly true. Reviewing contracts and recruiting is harder to hand off to an inexpensive third party. I wish it were not.

I like it when I see a founder team that is resourceful, has range, and can do a lot of this stuff themselves. I like to see them running lean and mean and spending money on the things that really matter (product!!!!!).

But at some point they need to start delegating this stuff. And first time founders often make the mistake of waiting too long to take things off their plates. For one, they like the control and insights they get from doing things themselves. For another, they are often lean to a fault (penny wise and pound foolish).

Knowing when it is the right time to start handing things off and hiring is an art not a science. It has something to do with the availability of resources. And it has something to do with the scale of the organization. When the CEO is still scheduling her own meetings when there are over fifty employees, something is wrong. Investors can help a lot. We have pattern recognition. We can see two very similar companies (size, stage, etc) and compare how much delegation is happening in one vs the other. We can make suggestions.

One suggestion I frequently make is to find a “utility infielder” for your first business hire. This is someone who can do a lot of things well but nothing spectacularly well. This is often someone who has done this role before in a startup and likes working in companies that are between five and fifty employees. There are people who make a career out of this job. It is lucrative if you value equity over cash compensation. You can build a nice portfolio of early stage equity grants doing the “first business hire” gig for two or three years at a time and then doing it again and again.

Doing a startup is an evolution from DIY to Delegate. And timing the evolution is important. If you haven’t done it before, ask people who have for advice on this. Allocating your time (your most precious resource) is critical to the success of your business.


Comments (Archived):

  1. Chimpwithcans

    Has there ever been a successful startup which has not eventually required delegation?

    1. Chimpwithcans

      Nice post btw 🙂

    2. fredwilson

      i do not think so

      1. JamesHRH

        PlentyofFish in Vancouver.

  2. Supratim Dasgupta

    Fred, So the skill to look for is Multitasking & the attribute to interview for is ‘Jack of all Trades’. I wish there was a Job Description for ‘utility infielder”

    1. fredwilson

      here’s a startcan do the following:pay billskeep bookshandle payrollhandle contractsdo bus devhelp with recruitinghelp with offer letterstake “first meetings” for the CEOstrong project management skillscan do attitudeself starter

      1. Supratim Dasgupta

        Thanks Fred. Roughly for a 2 person startup how much salary and equity do you see paid for positions like this?

        1. fredwilson

          i wouldn’t hire this when you are two peoplei would wait until you are 5-10i would keep doing this stuff yourself for nowwhen it is time, i think the job is $100k and 1% (ish) depending on where you are locatedfred

          1. Erin

            This is so useful.

          2. Supratim Dasgupta

            Fred, I think $100K & 1% is good. Except some VCs think the founders shouldn’t draw more than 100K until the startup makes a profit. in which case the utility infielder will have a hiher salary. Do you have any past post on founder salaries or Startup salaries?

          3. Brandon Burns

            Angel List is probably the best resource for startup salaries.

          4. sbmiller5

            Pretty much everyone should have a higher salary than the founders. Especially pre-series A.

      2. Mroberhozer

        Is it weird that my first reaction is “this sounds like an awesome job”? I’m not a dev and not a CEO-type. I’m more of a “mile wide and inch deep” type person that thrives on the un-sexy, behind-the-scenes work that makes the place tick. I just never knew how to describe it, so thanks.

        1. JamesHRH

          Not weird. Just a good fit for you!

      3. David Semeria

        Great list Fred. But those of many of the qualities you would expect to find in a founder.

        1. fredwilson

          exactly. and that is why the founder does this job at the start and often holds on to it for too long

    2. Chris Phenner

      A former boss once referred to me as a ‘Swiss Army Knife,’ and I think a first Business Development hire is a proxy for Utility Infielder (or it has been with me).

      1. Supratim Dasgupta

        Yes, if the Bus Dev Exec has startup experience. If he comes from a large corporate he will want to do none of jobs except core BD work( he wil want to delegate his expense reporting as well 😉 )

  3. pointsnfigures

    I am a delegator! I trust people to be able to accomplish tasks. I don’t know why I wound up that way. It has hurt me because people will take advantage of my trust.

    1. JamesHRH

      Some are by nature. You didn’t turn out that way, you are that way.Enneagram 7 FWIW.

    2. LE

      It has hurt me because people will take advantage of my trust.If you trust people it’s probably because you don’t have the particular experience and know enough to avoid those that you can’t trust. The telltale signals and so on. More or less the point of my other comment “learn how to know” if you want to call it that.I would imagine that on the trading floor, something you know about, this wasn’t an issue?

  4. Chris Phenner

    I love the Utility Infielder role (and career); I have played this role at least five times.I’d like to think I do a thing or two spectacularly well, but in the earliest stages, it takes a lot of DIY in addition to whatever one is ‘spectacular’ at (or maybe one finds a new thing).I will spend some part of the morning editing video (a first, at age 42), and while 100% unsure I am good at such a task, I like that that I can say that I have done it.And boy do I wish that contracts were simpler and that there was a ‘Fiverr for Deals,’ perhaps like offers scheduling services — maybe someday.Thanks for calling out the Utility Infielder, as I know and like lots of us.

    1. fredwilson

      such an important role early in a company’s life

      1. Chris Stephenson

        As colleges and universities expand their entrepreneurship programs and curricula, they should offer “Utility Infielder” as a track. Not everyone wants, or was meant, to be a CEO or even a founder. Creating an army of these people would help us manufacture stronger startups faster.

        1. Supratim Dasgupta

          Its no doubt a very important role, but IMO it would be very difficult for colleges to make it look important that people pursue it as a career

          1. JamesHRH

            That’s the problem w current system – it sells outcomes that are not connected to the person who chases that outcome.If you know who you are, your long term prospects have a much lower risk profile.

          2. Supratim Dasgupta

            Totally agree with you James! Not just in the US, I have seen the same in India as well.

        2. JamesHRH

          I agree.Most Utility Infielders have the most important thing in life in spades: self-awareness.20 years ago I learned that most NHL enforcers / goons were the smartest guys on the team. Why? They figured out it was their only likely path to the pros without having someone tell them (at age 15).They assessed themselves, their desires and the requirements – at age 15 – and got to the dirty work.

        3. LE

          The name is really a non starter. Just as easy to find something that sounds more important than that. I’m not a sports guy but even I know that’s a subtle put down similar to “jack of all trades, master of none”. Society is all based around “best” and “top” not celebration of people who are well balanced simply because there is no way to measure and rank that type of thing.”Utility” doesn’t work in this type of context.

          1. Chris Stephenson

            100% agreed, hence the “quotes”. IMO there is a title/job description that is worthy of the importance of this role, and a skill set to bottle, document and teach. “Venture Management”, etc. Word smithing would come later. Its the concept i was focused on. Although it’s nickname (thanks to JamesHRH below) should be “Enforcer” 🙂 I’d also argue that a US President’s Chief of Staff role is another interesting analogy. Confidant, enforcer, garbage person, chief bottle washer…

          2. Tim Huntley

            How about Consigliere? 🙂

          3. Chris Stephenson

            you see, I knew someone would get where I was going! 🙂

          4. Brook Shepard

            Well nobody in school wants to Joe McEwing. 22 YO’s think they’re geniuses.But at this point in my career – 38, own the business, 13 employees, profitable but no hockey-stick growth – I’d LOVE for my next job to be Utility Infielder. I’d be good at it, I’d enjoy it, and I’m pretty sure it’d be win-win.

          5. Chris Stephenson

            Apparently (I dont have the latest stats), the number of new startups is actually shrinking over the last several years. And my sense is that most “business” students still opt for safer routes, seeking employment with hot startups or established businesses rather than brave it on their own. If the role had a professional name (there’s power in a word!), it could have legs. But regardless of where this “skillset” is taught or honed, people of your ilk are in great demand even if most startups don’t know it yet. Heck, I’ll be a group of former CEOs/execs could create a great business outsourcing this position for cash plus equity. Get in with the right VCs, it’s a no brainer.

          6. Brook Shepard

            Sign me up 🙂

      2. Mike Bestvina

        Curious – do companies with 5-50 employees routinely seek these people out? Perhaps any specific companies and people that come to mind @fredwilson:disqus ?

      3. John Gannon

        What’s your take on how that utility infielder needs to evolve / grow over time? Is it 2-3 years and out or have you seen these ‘infielders’ find long term homes within the startups that they’ve joined early on as the utility player?Also – would be curious on your thoughts on range of equity for said infielder.

    2. JamesHRH

      Ability to do things well (if not spectacularly) the first time you do it, is a spectacularly rare skill.Most people who are spectacular at something have done that things 1000’s of times and the first time they did it, they were awful.Someone who turns surprises / unknown into capably handled outcomes is invaluable in a startup.Ultimate DISQUS compliment: Like post followed by follow Commenter!

    3. ShanaC

      I love Amy. I Love Amy. I Love Amy.That is all. (amy is the AI of…though I think she needs a bit of a personality push, I still love her and want to give her a hug most days, however, I know of a few people who have worked with her that have blocked emails coming from Amy)(I’d kill to run’s marketing. I love amy)

      1. ShanaC

        (that, and because I think I know what would overdrive Amy’s adoption curve, but first you need to get Amy’s voice down)

    4. Rob K

      Couple of ideas about ‘Fiverr for Deals’- 1) Biz Dev people with experience often do ‘practicing law without a license’ pretty well (I am one of these…) and 2) I have had really good experience with major law firm partners who spin out, have no overhead, and charge 1/3 the big firm billing rate. Outside GC is one that comes to mind, but there are others.

  5. Brandon Burns

    Or you can be Instagram and never grow beyond 20 capable, trusted team members.My father always told me that one of the best insurance plans you can have in business (and life?) is one where you’re not reliant upon too many people, for their performance will often disappoint.

    1. JamesHRH

      He was right, but that doesn’t scale.

      1. Brandon Burns

        Very true, 99% of the time.Instagram grew a service with massive scale. They just figured out how to do it without scaling the team.Granted, IG is the exception rather than the rule. But don’t we all strive to be exceptions anyway?Army quote: “Aim small, miss small.” Meaning when aiming a gun at a target, if you aim at the person, you might miss the shot by a person sized margin and miss your target. But if you aim smaller, for a button on the shirt of a person, you might still miss, but likely by a mere button sized margin and still hit your target.Aim to build a company that needs only 20 employees, maybe end up with 200. Aim for a company that needs 200 to function at scale, end up with 2000.I’d rather aim small and miss small.

        1. JamesHRH

          QB mantra for throwing over the middle too.

    2. Matt Zagaja

      I double checked to make sure this wasn’t a post by Larry 😉

      1. Brandon Burns

        Larry who?

        1. Matt Zagaja


          1. Brandon Burns

            Just checking. :-)And I’m sure he’ll chime in soon!

          2. Brandon Burns

            BTW, do you code at all? There’s a data-y project that, given your experience, you might be interested in.If so, PM @Burnsey on Twitter and I’ll shoot you my email.

          3. Matt Zagaja

            I’ve been known to code 🙂

          4. Brandon Burns

            PM received, email sent.This is may favorite part about AVC. 🙂

  6. Nicolas Rodriguez M

    Fred, I think you are talking about the Office/Everything Manager, Mark Suster wrote about it some time ago and this article of yours made me read it again:http://www.bothsidesoftheta

    1. fredwilson

      i don’t think of this as an office managerin my mind that is too limiting

      1. Nicolas Rodriguez M

        Agreed, just thinking in the first version of it for a very small scale. I own a very small company with 8 employees and reading Mark’s article was like reading my mind, we need someone to take small things away from everyone so we can focus (product!). Next phase will be a person that manages higher level stuff.I’m also learning to delegate, its like learning to walk again. Step by step, much pain.

        1. LE

          Good luck with finding that person in a small company. [1]This is not the same problem though with VC or angel funded startups of course. In those situations there is the implied brass ring or future reason to stick around that will keep people in the game. The chance of a chance of hitting it big. Plus the people working there are more cohorts than in a traditional non funded 8 person company located in nowhereville.This is also by the way why a small coffee shop (or retail store probably better example) can’t typically hire the same quality of people that a Starbucks (or a retail chain) can. The mere fact that someone can rise to a higher position is enough of a reason that the higher qualified people will work at Starbucks vs. another place. I’m not claiming this is universal or that I haven’t seen examples that prove the opposite. But on average it’s much easier to get good people if you have a future bone to give them no question about that.[1] The first time I was able to find someone that could handle things the way I liked (years ago) 3 months after hiring they were in my office wanting to get a piece of the business. Likewise anyone that I ever hired that I thought was really really good ended up leaving and starting their own business. So I decided in many cases not to hire people who were to good knowing they would leave. Likewise with attractive women the attractive women also typically went for greener pastures.

          1. Nicolas Rodriguez M

            Been there. Sucks to miss like that when hiring, but what else can we do? Also, you might only need 3 or 4 people above average to gain critical mass and be able to defend your team from outsiders (for some time while nurturing new team members).When I read people like Fred it seems everyone is as smart as he is but that is not true. Just realize how hard is to grow skills/network with all this tips and books telling us the right direction. It is hard for everyone and most people give up easily.

          2. LE

            Something to keep in mind: Some of the people who are able to get beyond that obstacle are either just very good bullshitters and/or are able to sell some stupid dream that they themselves actually believe. So they have the conscience to tell people what they want to hear and promise them the moon which keeps them around. And some of it actually happens all depends on what allows you to sleep at night.

      2. JamesHRH


      3. pointsnfigures

        Utility infielder is good description. 6th man. Special teamer.

      4. LE

        The title alone of “office manager” is a non starter and is not going to attract the right person in the role. Banks figured this stuff out a long long time ago.Back in the day this was typically called “girl friday” in advertisements.

  7. JimHirshfield

    One way to look at delegation is, how much is your time worth (per hour)? Could it be done by someone else at a lower cost. How do you assess what your time is worth? Well, for individuals in established positions/companies, it’s income/hours…ie your inferred hourly rate.For a startup, a founder will quickly realize that their time is extremely precious (altho we all have time) and their financial resources extremely rare. And so the math is confounding…{zero income} / {all the time in the world} = $0 value of founder’s time :-/…ergo DIY, ’cause no one else will do it for less.

    1. Matt Zagaja

      Yep, agree. People don’t always think about absolute v. comparative advantage. Many CEOs or entrepreneurs are smart and will have an absolute advantage over others in doing many things, but they really need to be concentrating on the things where they have a high comparative advantage.

    2. LE

      It’s actually more than “what your time is worth” (even though I said something similar).Meaning your time is fixed and if you are a startup you have definitely typically more time than money. So you can afford to pay a premium in many cases over even how you value your time.The other side of it is “how important is the problem you are trying to solve”.While I was writing this comment the electrical contractor knocked on my office door because they were going to install a security light in the back that I had taken the time to order and specify. And it’s important enough that I am going to personally take the time to make sure they put it in the exact place that I think is important to provide the most security. [1] Likewise with a condo property’s “sign policy”. I wrote that myself taking many hours because it’s an issue that is important to me so I would not ask someone else to do that job I have my own ideas on what the policy should be. (And it was rubber stamped by everyone nobody had the time to dispute anything that I said which is typically the case..)[1] As in “I want pipe don’t give me bare wires that someone can cut” as a small example.

      1. JimHirshfield

        “And it’s important enough that I am going to personally take the time to make sure they put it in the exact place that I think is important”Can never be too careful with where and how they handle your pipe, even if it is a “small example”.

        1. LE

          “pipe” – Is that some kind of drug reference? Because before I got remarried a few years ago I didn’t even know what 420 meant.Oh, no, it’s not drugs. It refers to “member” size! [1]Good one. 10/10 on the HFS for that one.[1] By the way when you are satisfying your women does she have to DIY because you delegate?

          1. JimHirshfield

            You always appreciate the dirty humor, altho I strive to keep it clean here. Thanks for the 10 rating.I’ve got to _hand_ it to you, your DIY sex joke tickled my funny bone.

          2. LE

            _hand_Shows the difference between humor in writing and humor in person.In person if you have a bunch of people in the crowd, and even if only a few people laugh, the ones who don’t would quickly realize the emphasis and that they missed something. But in writing it’s different. Took me a while with your jokes to get the emphasis.That’s why, when reading your jokes, it’s always important to strap on your brain. My personal preference is no hinting takes the challenge out of it.

          3. JimHirshfield

            You said “strap on”.

  8. msuster

    Yup. I have this conversation with entrepreneurs often. It runs from scheduling meetings to booking travel to doing Quickbooks.My message is always, “You’re the single most valuable person [people] in the company and we need you working on the highest value tasks. Meetings, travel and accounting entries are not them. Act your stage.”As you can imagine I put it into writing as well. Hope you won’t mind the link since I covered same topic: http://www.bothsidesoftheta

    1. JimHirshfield

      “Act your stage” <— love it

      1. LE

        Great title for a book as well. Seems that Marc invented that phrase not finding other references to it.

        1. JimHirshfield

          If I know you, you’ve already registered the domain.

          1. LE

            Nah I have my own ideas but as it happens that is already registered (I did check that) back in August 2014 by these people: of the ways I check and see if a name is unique is by seeing if it’s registered and when it was registered. Assuming it hasn’t dropped and was re-registered it’s a simple “poor man’s” indication of how long something has been around for. Also whether it’s been grabbed in .com .net .org .info or only .com.That said if it wasn’t registered I would have registered it. Very little downside plus I liked it (as you did). Probability of reselling is actually quite slim (it’s a numbers game perhaps less than 1%).

          2. JimHirshfield

            Hmm, I hear ya. Just checked out the site, and logically, it’s about acting…stage acting perhaps. A much more appropriate use of the domain/pun, IMHO.

          3. LE

            Suster’s phrase and you get more upvotes.My observation is this is how disqus (on AVC) differs from, say, comments on HN. On HN longer comments appear to get higher upvotes. Short comments one liners and jokes typically don’t.

          4. Chimpwithcans

            If anyone on AVC were qualified to judge a pun…it would be you, methinks 🙂

          5. JimHirshfield

            Many thanks.

    2. JamesHRH

      What is cool about act your stage is that it applies Up and Down.Some startup people are natural delegators and need to dig in to the DYI mode to get to liftoff.

      1. Matt A. Myers

        Wouldn’t this be because you need to more deeply understand what’s needing to get done?

        1. JamesHRH

          Yes.But the rubber has to hit the road & nothing provides more insight than the experience of doing.

    3. ShanaC

      How about maximize your value? Derisk yourself?

  9. Paul Yantus

    I’ve been in startup, small, medium, and large companies and you learn fast as a leader that the smaller the company the more you must do yourself. The only exception is a well funded startup. When you have solid funding you can focus on the bigger things.I think this is also the reason why many leaders struggle through the transition from small to larger.

  10. Guest

    This is just a tremendously well articulated post. I had this role and was lucky enough to evolve into a couple of other roles at the company as it grew and no longer needed the Utility Infielder. That is another interesting point that I’ve seen and experienced – it can become difficult to know what to do with those folks after the company grows into a team of specialists. It takes a patient and understanding Founder/CEO to extend the time necessary to that Utility Infielder to become a specialist in a new role, and of course there has to be a role that interests the Utility Infielder.But a great great post about a topic that is so important to early stage companies and entrepreneurs and rarely discussed.

  11. David Miller

    Sounds like you just met one of your new portfolio companies for the first time 🙂

  12. jaredhecht

    You could write an entire blog post on the attributes of the “utility infielder.” I think it’s a critical role at the early stage. I generally view this as a problem solver with super high aptitude that is able to fill critical holes in the business as they emerge. This can span from general ops/legal, marketing/customer acquisition, bd, project management, product management, etc.

  13. Doug

    Delegating is a skill, don’t sell it cheaply. You have to learn how to delegate, provide feedback and be sure what you have asked to get done actually gets done. On top of that, you as the manager have to be OK if it is not done exactly the way you would do it. They may also do it better, which can bruise a big ego.Learn to delegate, it is a skill worth having. For tech people it is especially hard to let go. Telling a new CEO, “delegate more” and not getting the feedback loop right will cause failure. Then they blame delegating and work themselves into an early grave.When I was struggling with this as a new team leader, I searched for books on delegating. There are very few to be found, more on Amazon now.

    1. JamesHRH

      That is why some founders bail on being CEO.They don’t like the job and the work it requires.

  14. Pete Szymanski

    Great advice. This is a pain point that is one of the hardest to tackle for a startup or growth company… because it requires trust. After all, entrepreneurs can stay focused on their vision and the good ones plan, execute and build. But one of a CEO’s unquantifiable roles is to maximize leverage on resources, which includes finding the right person to play the right role at the right time.A startup in year 1-3 is much different than 4-6 and 7-10. Because more is certain, there is a process to find people in stage II and III. But it takes a certain kind of preneurial passionate professional to be trusted to work with a variety of teams on interesting yet challenging projects consistently and successfully — second+ time successful entrepreneurs and smart investors especially seem to know to seek out these resources.

  15. LE

    And hiring a bunch of people to do things like schedule your meetings, answer the phones, keep the books, review contracts, interview candidates, etc is a bad idea because it uses up money which is always in short supply at the early stage of a startup. You can, and should, see if there are service providers who are inexpensive who can help. Bookkeeping is one area where that is certainly true. Reviewing contracts and recruiting is harder to hand off to an inexpensive third party. I wish it were not.Part of this (not hiring at the start) is also part of learning and developing a seat of the pants feel for things.It is necessary to have a basic understanding of many facets of your business so you at least have some clue if the people that are doing things for you are capable or not. And you can step in if needed or in a pinch. Or know or guess the right direction if they are not available to answer a question.As only one example, I can’t tell you the number of deals that I have been involved in that if I wasn’t able to make a change or review a contract myself w/o an attorney involved, would have never happened.That came from actually spending time in the past with contracts and reading them and asking questions and of course figuring things out. This relates partly in a way to the saying “time kills all deals” which is probably more true today than it was in the past. Most importantly if you take the time to learn and have a seat of the pants feel for things you will have a basic feel of the risks that you are taking by not relying on a third party to tie everything up in a bow and bless it for you.

  16. LE

    When the CEO is still scheduling her own meetings when there are over fifty employees, something is wrong. Investors can help a lot. We have pattern recognition. We can see two very similar companies (size, stage, etc) and compare how much delegation is happening in one vs the other. We can make suggestions.I would like to agree 100% and point out what a powerful statement this actually is and how important this concept is.Part of the reason that many people don’t delegate, and they DIY, is that they are able to do things up to, what I would call arbitrarily, a “85% quality level” all on their own. (Scheduling meetings is not really an example I’d use only because anyone can do that obviously. Better might be “finding the best scheduling software for the company to use”.What that means is that they are capable of doing themselves, or figuring out, many parts of the business and can do them quite well. So because they “can do” they have really less need to delegate or ask others for help. They actually enjoy doing those different things so it becomes self reinforcing in a way.Unless there is an intervention (which is what you are suggesting) they will continue on that path. So you are right to press on this issue and break them from the habit at the appropriate time.As an aside this is the difference between what I will call “single function machines” (people) and multiple function machines. The single function machines tend to be able to do only 1 or a few things very well and they stick to those things. The multi function machines do many things and their abilities prevent them from, and this is important, getting into the habit of using others for things that they can do themselves. There are pros and cons to both behaviors btw depending on the situation as anyone in business can tell you.

  17. Mike Chan

    Trust is the biggest factor here. If you have the confidence that someone will execute those delegated tasks well, then you’ll be able to delegate more frequently. Forming that trust goes all the way back to how good your hiring process is.

  18. LE

    Allocating your time (your most precious resource) is critical to the success of your business.My very general rule would is typically to pay for anything if the cost of doing so is what I consider below the opportunity cost of my time. (Among of course other reasons depending on the particulars).On a business level, an example of this is relying on a resource that isn’t overpriced but I know will get the job done. And I pay more for certainty as well. In other words provide a turnkey solution to a problem in a workmanlike manner. The hard part of course is not paying the money. The hard part is having the correct resource to contact. In a past business one of the ways that we increased sales was simply being that resource. We didn’t have the best pricing (we were actually high priced) and our quality was not the best either. But when you contacted us you didn’t have to think at all. We took care of everything and made your job easy. That alone was enough for us to keep the work and customers wouldn’t even consider going elsewhere (and we were able to increase our prices well over the initial “get in the door” bids). (You know showing up is half of sales and all of that..)On a personal level I’ve been able to follow same strategy for a long long time. So for example when my wife needed the basketball net assembled in the driveway even though I could do that myself I wouldn’t even consider spending the hours needed. [1] I simply found a handyman and they were paid maybe $75 and spent a few hours to assemble.[1] From the first time we met I made it very clear that I don’t spend my time on things that I can pay others to do (unless there is some other reason to do so which there sometimes is). Because there are a zillion things that I need to do which I can’t pay or find anyone else to do. So don’t ask me to do something that someone else can do.

  19. someone

    another bad delegator here. it’s one reason I moved from management to academia. I am not sure whether advice & tips would help … doesn’t work for some personality types

  20. William Mougayar

    yup. The biggest dilemma first time managers face is not knowing how to delegate, fearing to delegate, and when to delegate. Delegation is really about managing your growth. It’s part of it.

  21. Jon Michael Miles

    The first company I started and ran, the partner / investors had that insight. They called it Founder’s Trap. It had been brewing a while in my gut, and that comment flipped the switch, like someone pointing out a dust bunny on a clean floor. The balance of doing vs. observing others do is a tough one. You’re right about control and insight being tied together.I would caution founders from over-delegating though. Dangerous business that.

  22. John Revay

    Hi my name is John…. I am a DIYer….,In honesty I am great in early stage companies, I wear a lot of hats…and generally get stuff done. The interesting thing to keep in mind is as the company grows, roles and responsibilities change, the key in my sense is keeping communications open and honest so when that day comes – every one still is engaged and feels good on where we are going…..

  23. Kevin Williams

    I love the “infielder” title- may add it to my LI profile!I’ll add my $0.02 having done this for 5 start-ups in the last ~10 years. I’m usually the “first business hire” after a charismatic founder (often technical) and take a title like VP of Ops. My job is to stabilize the organization, bring discipline into process and, simply, get things done (ship it!) while the CEO focuses on funding, board management and higher-level strategy. I hold a pretty solid MBA, a PMP and smattering of other credentials but real tasks have included-The Obvious:Bookkeeping (outsourced)HR Duties (payroll outsourcing, benefits, compliance)Facilities managementContract reviewProject ManagementProcurement (everything)PPT Deck creationEngineering managementTrade show set-up and managementThe Less Obvious:-Learning to weld (had to ship, contract manufacturer lost his TIG welder)-Meat packing (ugh)-Tire installation-Carpentry -Diesel repairs (generators, trucks)-Department of Transportation compliance-FDA compliance -FAA compliance-DOD export controls compliance-OSHA compliance-Patent filing and maintenance-Working metal lathes-Salesforce implementation -Care of a baby porcupine and, briefly, a baby elephant (not kidding)-Website creation (right now, learning php & JQuery)-IT set up/design/outsourcing-Supply Chain-Product Quality Contro-Grant filing-H1B Visa filings-Police liaisonAm I particularly “great” at any of this? No way, I don’t do any of it enough! (although I thought that I had a knack for exotic animal care…) Nor should I be doing most of it- if you see me with a TIG welder or large greasy wrench in my hand, something has gone horribly wrong. BUT- sometimes, It. Must. Ship.How am I compensated? Honestly, pretty well with a big-city salary and no less than 1% straight equity and some sort of nice options (which often don’t pay out). Sometimes I get paid more than the CEO (remember they usually have the equity…). I am NOT however a secretary or dogsbody- the CEO makes their own travel reservations (usually) and schedules their own meetings. My companies are never THAT big…Frankly, it’s an awesome job (every day an adventure!) but super high risk and high stress. That works for me but it definitely doesn’t work for everyone. I happen to thrive on change and love acquiring new skills.

  24. Guest

    I struggled with this as a manager as I was officially getting people assigned for me to oversee. 3 years ago, I had a hard time making sure others in my team were feeling useful. I had the tendency to go in and re-do people’s work which clearly does not make others feel good and helpful.I was forced to “get better” as this behavior started to affect other parts of my life. I was the first in the door and the last to leave. Was sleeping 4 hours in average and did not take a vacation day that first year… It was not healthy at all. So I forced myself to refrain from this, I looked for trivial things and evaluated whether this or that was a thing I could let go or not, and that helped.What made the biggest difference for me was, I started to trust more others as I got to work closer with them over a period of time. The same made me more effective at giving feedback. Things became easier.I realized I knew all along to let go. I was just focusing on the wrong thing. Instead of working on communicating better with people and getting to know them and trust them.I went around and re-did things. Trusting people to yield results the same way you would have done something is a magical thing. Just takes time.

  25. matthughes

    Props for the utility infielder reference – love it.I’m a huge believer in delegation.Hire smarter people than you – let them do their jobs.

  26. Matt A. Myers

    It’s something you learn – to move from DIY to delegating – and I imagine is the same process as an entrepreneur/founder learning to become CEO. It’s constant learning as roles constantly change, however I see and feel that I am improving holistically – so the process has an exponential growth aspect to it.Anastasia, girlfriend and co-founder, has been an invaluable help when it comes to filling in resistances I have and helping things get done. Likewise she has the areas she’s less comfortable with and learning. And we’re definitely both learning to work with each other better. It’s going really well – and it’s been very challenging – but our baseline has always been an improvement post-challenges.It’s just the two of us + an outsourced developed I’ve been making mockups/specs for. It helps that I’ve been doing UI/UX for decades, and Anastasia really well complements all of the pieces I have no time for and don’t particularly love doing.

  27. Twain Twain

    A prescient and perspicacious post.The wisdom in the images attached share several truths with us.I was a hyper-DIY kid who liked to be able to do EVERYTHING that sparked my interest; so much so, it became an internal competition, “Wow, IMAGINE if you could do that! Ok, you better go learn how to do it!” Yet I was also the kid who was Captain of Sports: so believes in the value and principles of teamwork and that one of our roles in life is to “free the flow of the ball (ideas) and pass it forward so we or someone else can hit it out the park / score the goal for the whole team”.This is probably why I love hanging out on AVC because there are so many great people enabling the free flow of the ball (ideas), passing it forward and hitting it out the park with their insights.I grew up, went to work in big and small companies and loved collaborating and delegating with others. I learnt from my role models that leadership is about doing a great job with whatever project you’re delegated (no matter how trivial or menial) as well as about knowing when to delegate (like asking the qualified accountant or lawyer to do what they’re professionally trained to focus on and love to help you with — even when you know you’re perfectly able to draft P&L and write the contracts because you too went through school and training to learn how to do it or giving the developers the Roadmap for the product build and its code specifications even when you’ve been coding since you were a pre-teen.Yes and it’s true no algorithm in the world that does “pattern recognition” on resumes and skills sets can tell us what’s in the heart and soul of someone that makes them a phenomenal colleague and future Global Head. We meet them, interact and FEEL their magic potential. I know this because I was on the interview panel for a guy who became one of our Global Heads — mind you, of our team of four, two became Global Heads, one is CEO of a London Stock Exchange platform and then there’s me (the little ant-bee, haha).Yet for all those experiences of flexing between DIY+Delegating, in the most recent few years I found myself in unchartered waters with no Standard Operating Manual.There was an idea I needed to execute and a system I needed to build and there was no one I could delegate the responsibility of that invention to. It simply wasn’t possible to outsource that part of my knowhow, skills set, heart, passion and authenticity-integrity of the system to someone else.And I did a fairly exhaustive assessment of whether I could find people on Quora, ODesk, Elancer, Github, Stackoverflow, Open Source community etc. who’d previously built a system similar to what I had in mind.End result: out of necessity I had to DIY my system invention.I should proviso this with the fact I spent $$$ (enrollment fees and 3-months living expenses to be in the States) to go to an incubator in the hope I’d meet people I could delegate building the invention with. However, the incubator wanted me to build a variation on Disqus and this simply wasn’t what was in my head, heart and soul to build so we agreed the arrangement wasn’t going to work out and parted ways.After that, I decided not to burn $$$ on getting into incubators but simply go with building as much of the product and invention as I could.As Bob Marley and Confucius said, “You never know how strong you are until being strong is your only choice” and “He who conquers himself is the mightiest warrior.”Having survived (and even thrived) during the process of DIY out-of-necessity, I understand their wisdoms even better. The value of insights gained about our own strengths (can do’s) and limitations (can’t do yet) is of a multiplier factor.I’m really looking forward to the time when I can focus on setting the vision & strategy whilst others do and fulfill what their expertise is in which is better than I can do it.After all, vision & strategy was what I focussed on in CEO-Chairman’s Office at the bank working for the Global Heads so it’d be a pretty great “coming full-cycle” in my adventures.

    1. ShanaC

      learning when to cycle between them and when to pull back from delegation is a skill in its own right

      1. Twain Twain

        So true. I’m constantly having to learn and re-learn WHEN.Maybe there’s some sort of pain point parameter that enables us to time the whens?

        1. ShanaC

          Something I am realizing – it isn’t a pain point – it has to do with how relationships work and boundaries work. The pain points arise from how these relationships and boundaries are put together.

          1. Twain Twain

            A-ha, that’s the intelligent approach!

  28. chuckf75

    Interesting take on needing someone to schedule meetings if you are above 50 people. I have over 200 people and almost always schedule my own meetings as it can be done with a few keystrokes. Yes I have a couple of administrators to help me but my computer is my assistant in most instances!

  29. Mike Hart

    As a former CEO and long time CFO, I particularly enjoy the “utility infielder” role in early stage companies. The teaching/mentoring/doing combination is very rewarding. Compensation is a different story.

  30. ShanaC

    I realized recently – I love solving problems and getting my hands messy in lots of diy – but I alos love delegating. Why?I get too tired otherwise. I’m only human. And I think everyone needs a reminder of that. It is scary how often I try to ignore how human I am – and it always bites me in the ass. So if I can delegate, whether via a tech tool or get help from a friend or working with another person, I’m now actively trying to get it. Because I shouldn’t live exhausted, i should live happy.

  31. David Waxman

    Definitely agreed on the utility player role, though it’s often a tough transition when the company matures. Many don’t realize that it’s usually a short-tenure job. Also, appointment setting and basic admin is a total time suck and can be handed off to a virtual assistant for a fraction of what it costs to hire someone in-house. Zirtual does a fantastic job at this (full disclosure: I’m an investor, but was a customer first).

  32. Mike Bestvina

    Great insight on the “the three things every CEO does”. Thought I’d share the three things were taught to me several years ago:- Create the vision- Control the energy – Coach, don’t play

  33. Rob K

    What a great post and thread. I found it really tough to balance especially when there were things that needed to get done, but I knew they weren’t the highest value add for me.

  34. Rob K

    Interesting that most biotech startups have a Chief Business Officer during the first year or 2. We in tech should take a look at that model.

  35. Pat Clark

    [Baseball dork comment alert] The prototypical MLB utility player that often comes to mind who plays all over the field and can do a little of everything in Ben Zobrist. Though not paid as well as the stats dictate he should be, advanced metrics (Wins Above Replacement; WAR) place him at one of the top 5 most valuable players in the sport over the past four years. Interestingly, it seems as though smart sports teams are starting to recognize, and pay for, the value of utility more frequently. Are startups doing the same? A good read from this week on the concept:

  36. Jim Borden

    Some great words of wisdom that I wish had heard about 10 years ago! Thank you for your insights.

  37. CalebSimpson

    Really enjoyed this read. I have been good at delegating as my business grows, but there have been some key important tasks that I have been holding on to, duties such as depositing checks and ordering raw goods, all things that take up hours out of my week. It’s my goal to have all of these things delegated by May so that I can free up my time to grow the business, rather than just working IN it.

  38. Sean Hull

    Sounds like a generalist.Good at getting hands dirty, good at understanding all the roles, and good at teaching, delegating, and letting go too.

  39. Rick

    You guys are more experienced than myself but I’d like to give a different view:”CEOs must delegate. At scale, they should only do three things; set the vision and strategy and continuously communicate it, recruit and retain the very best people, and keep the company funded.”I think it’s best for the start up to have founders – CEO, CFO, CTO, etc. – only focus on setting vision, strategy, recruit, and find funding from the very beginning. I think lean, bootstrapping, shoestringing, etc. all put the start up at high risk of failure! I know that adrenaline flows highest doing the lean etc. thing. I’ve done lean myself. But that’s something that benefits the founders not the company. For example… When a large corporation starts a new division. They don’t put 3 employees on it and tell them to spend their money and the money of thier friends and family. I’m pretty sure if that was best. The corporation would have the division staff tap into friends and family for funds. Instead the corporation is there to provide funding most likely though capital from banks or current cash reserves or other forms. I knwo there is an issue with founders spending too much. But that’s a problem of founder behavior NOT of company structure and proper start up process.”But when you start a company, you (and your cofounders) have to do everything yourself… And hiring a bunch of people to do things like schedule your meetings, answer the phones, keep the books, review contracts, interview candidates, etc is a bad idea because it uses up money which is always in short supply at the early stage of a startup.”The founding team should be assigned tasks by the founder that was chosen to be CEO. Each founder should have certain expertise that is different than the other founders, including CEO, and that expertise should be applied by the CEO to the proper tasks. The difference between founders drawing a salary and founders not drawing a salary is just the idea that lean is good. But I’m not so sure it is. People hired to schedule meetings, answer the phone and other mundane tasks are called perks. Spending on perks is bad behavior at a start up. Hiring professionals to do accounting, legal, and other necessary tasks is the proper way to build a great biz! The cost of that work should be small at a small company like a start up and is good spending. The real problem is money being in short supply. Start ups should get the funding the need first before trying to build something that is just an under funded thrill ride.”I like it when I see a founder team that is resourceful, has range, and can do a lot of this stuff themselves.”It’s not really about being resourceful it’s about getting the tasks done properly to help strengthen the company. If the CEO is a professional practicing accountant and a professional practicing lawayer and etc. then they aren’t going to be working at a start up. They’ll be funding a start up with the money they make doing those things. So when you have founders that are not professionals at a particular task doing that task it is being done half-assed. When money is low many times founders do all those things but again many of those tasks are being done by a non-professional and thus being done half-assed which makes the company weaker. You don’t want a non-lawyer doing your contract reviews because a non-lawyer will not be able to do it best. Again spending money properly is not about being low on cash it’s about proper behavior. Being low on cash is about failing to plan properly and doing a start up before you’ve secured correct amounts of funding.”But at some point they need to start delegating this stuff. And first time founders often make the mistake of waiting too long to take things off their plates.”The proper time to start delegating is at the begining. As Drucker said you focus on your strengths not your weaknesses. If you focus on your weaknesses you become mediocre at them. But if you focus on your strengths you become stellar at them. If founders would start delegating at the start then they would be building their delegation strengths and they would not ever get into the trap of not being able to let go of tasks. It’s like teaching a child bad habits then complaining when you can’t get them to stop.”Knowing when it is the right time to start handing things off and hiring is an art not a science. It has something to do with the availability of resources. And it has something to do with the scale of the organization… Investors can help a lot. We have pattern recognition.”Again the right time is from the very beginning. But, yes, it has everything to do with having the resources, funding, to use. There is no reason to put in place bad habits just for the sake of investors not wanting to take a risk. If the funding is there at the beginning the investors won’t be investing in a weak business with many bad habits that now must be stopped at a cost to the investor! No investor wants to invest in a business that isn’t able to lose one or more of the founders and still be able to operate. The ability to recognize bad patterns should be a strength of the start up team. Spending on outside expertise to help with the task is fine but if those bad habits were not learned in the first place they would not need to be fixed later.”Doing a startup is an evolution from DIY to Delegate. And timing the evolution is important.”But a start up should be an evolution from delegating to being better at delegating. The timing should be start immediately doing what you’ll be doing into the future so that you can be better at it when the future gets here.I want to mention again that Fred and others have more experience than I have. But we must also keep in mind they are looking at things from a different perspective. The perspective of an investor or maybe a hired advisor. From a business standpoint they don’t care if an entrepreneur goes bankrupt or commits suicide or builds a business that can only operate soundly if the original founders stay there for the duration. From a moral standpoint I imagine they do care. But we’re talking business and investors can’t force people not to start a business when the proper funding isn’t in place. People will do what they want no matter what other’s say.From seeing so many biz failures leading to suicide, bankruptcy, unemployment, etc. I contend that lean is not good. Proper funding determined through proper planning is the best way to start a sustainable business. It’s great fun to do software proejcts or invent products then put a biz around them and flip that biz for some cold hard cash. But I think its not good to suggest starting a biz and immediatly putting it into a cash starved situation through lean etc. methods. It is a good way to have others find markets and put their lives at risk while investors wait to see which ones will be prime for flipping. That way they can avoid risk and avoiding risk is paramount to being a good investor.I think start ups should be done properly from the start. That doesn’t mean a couple people shouldn’t get together program an app on their own then put it up on an app store to see if it will sell. That’s call market research. But that needs to be a small part of a larger plan. If the objective is to build a big biz. Then proper analysis of the funding required to reach that objective should be done and funding should be secured BEFORE going wild trying to reach that objective.Lastly I’m not saying people shouldn’t enjoy doing funtime start ups. But they need to know their objective first. Fund it properly. Then stay focused on the objective. People should not be taking out a second mortgage on their house do keep their start up going until they jump off the roof of their office building because they are financially ruined. We as a country have the ability to analyze business plans and safely fund businesses to become sustainable.

  40. Theo

    Trust when it’s come to delegation seems to be key. If you’re not easily trusting, it’s incredibly difficult to make the ‘right’ transition. Threw me a bit to say that you don’t think you’d be a CEO when surely trust is such an integral part of being a VC?

  41. fixmyprocess

    I think once you start delegating you begin to empower others that help you & they can grow professionally. Not everything others do for you will be exactly the way you may have done it; however, you are able to focus on higher-priority tasks. Also, a great byproduct of this is that you will have built a support system for business continuity in the event something happens and you aren’t available. An unrelated note – a neat self-booking tool I came across recently is (a “booking software that integrates with your Google calendar….so your customers can book you online”).