Scaling by “delegation” isn’t good enough


Founding a company is a selfish act. It will consume every waking moment for the next 1-10 years. It’s an act of defiance and irreverence towards competitors and the status quo. That matches well with the life of a 20-something — fueled by the energy of youth, too young to be jaded, with no financial or social dependents. Not all selfish acts are bad ones!

Young founders may fancy themselves wizards of coding, design, and salesmanship, because they’re individually excellent; I did! But it should be obvious that those skills don’t imply they can build a team of 75 engineers that balance quality with speed, or build an international sales team guided by principles other than overwhelming exuberance, or develop a consistent brand with a voice and adherents, or manage cash flows once the P&L becomes abbreviated “in millions.”

Introspective young founders appreciate this, and often the stated solution is “delegation,” as defined by: I’ll do it myself, then I’ll understand it, then if further investment is warranted, I’ll have the experience to hire and instruct a new person.

This is how I did it when I was young and naive, and I see the pattern repeated all the time. And it’s wrong.

The trouble with this form of delegation is it results in a team that is not materially better than the founder, at anything. Which is incredibly limiting for the company, and sadly quite common.

It’s actually a variant of the rule that if you think a certain position at the company isn’t useful, it’s because you’ve never worked with greatness at that position. When you’re looking for someone who knows what you know, you’re not finding greatness, you’re finding a substitute for your already-not-world-class performance, and of course you’ll get exactly that.

Whereas, as the founder, your job is the opposite: To build an organization in which each person is incredible and inspires others to become better. In fact, worse: To hire people who are better than you at every position, because only then is your organization increasing its strength and abilities.

This mistake compounds when you’re building a larger organization, because then the goal is even greater than individual excellence, it’s to built teams which themselves grow and create greatness. This is a meta or recursive problem: Not the founder attracting, identifying, and retaining greatness, but the founder building teams who themselves are doing that. This is the best definition of “team-building.”

Delegation isn’t team-building, and thus it doesn’t lead to scale, nor to greatness.

Scaling your business requires that you convert your initial selfishness into the empowerment of others. “Delegation” means you still own it but someone else does the work. “Team-building” means the team is trusted to own it, has obligations around that, can figure out and execute all the details, and is responsible not just for meeting initial expectations, but increasing their expectations of themselves.

This is where you achieve true scale in a company. Delegation is where you assign away lesser jobs so you can be even more heroic, because it’s still about you. But you’re still the bottleneck even if you’ve made that neck a little wider. Team-building means no bottleneck because the team can be as wide as needed. In fact the best teams measure their own necks and decide how and when to widen further.

This is where you derisk the company by moving from brittle to resilient. Through delegation alone, if one person gets sick, a deadline is missed. Or if someone leaves the company, a strategy isn’t executed. With team-building, you have group knowledge. Someone being sick or leaving the company gets baked into the plan.

The moment where you truly understand and embrace this concept is when you can turn the gun on yourself and realize that no one is exempt from this rule. It’s relatively easy for a technical founder to agree that she isn’t the best person to build a global sales organization, but is she ready to agree that even where she is excellent, it’s still her job to find people who are even more excellent, not just at individual tasks but at building entire teams?

But doesn’t this mean that ultimately leaders are managing a set of people, all of whom are better-qualified than that leader to do those jobs? And isn’t that difficult to manage, after all how do you argue with those people, and how will you earn the respect and confidence of those people? Yes, that is what it means, and yes that is difficult. And it’s your job, because anything less is by definition holding the company back.

So convert the selfishness and egocentrism of starting a company, needed initially to get the engine turning over, into an egoless, outward facing, empowering, team-growing organization, where your goal is for you to never be the most knowledgeable and experienced person in the room, because you’ve surrounded yourself with greatness, who each do the same.

2,325 responses to “Scaling by “delegation” isn’t good enough”

  1. Great article, Jason. I like your focus on the people skills and inspiration needed to grow a truly great company. That makes total sense and I can see the trap some leaders fall into by delegating all responsibilities away. The leadership responsibilities are often underdeveloped in young startup founders and the only way to learn is by experimentation or through listening to wisdom like the type you share here.

  2. Love this Jason, great way to reduce the ego and make yourself self-aware, I’m certainly very guilty of what you described, even now that we’re in a no-manager environment, I can still feel my brain wanting to operate in the way you’ve described.

    One question, how do you then go about finding great people, in fact better people than yourself, as you mention, without having any expertise in that area?

    • This is a difficult question, of course. This is an area where having a deep and trusted network is game-changing, because recommendations from those who *do* know are golden. This is one of the areas where a great institutional investors can add a ton of value, because it is (or ought to be) their job to stay connected to incredible functionally-excellent athletes. Similarly, although most recruiters are not this savvy, the very best (and most expensive!) ones are in fact this savvy, and this is why they deserve their exorbitant rates.

      For the more “bootstrapped” answer: I find that great people constantly surprise you. You should find in the interview that this is the case, and verifying their claims or ideas with others in that field or even things you read online should bear out those ideas. You should find they have specific answers to abstract questions, which indicate how they think about problems as opposed to you trying to verify whether their specific solutions are “correct.”

      Great people raise the level of the people around them. So another thing is to reference-check, but you’re looking for more than “yeah they do the job,” but rather you can ask “what did they teach you” or “how did they change the business,” and make sure you get gushing positive answers to those, indicating a force for change rather than just someone who technically does the job.

      For leaders, another great sign is whether the people who have worked for them in the past job or two want to work for them again, often in the form of literally wanting to quit their current jobs and come work for them at your company. It’s hard to generate that sort of fealty without being a super-performer.

      In the end, of course there’s no formula, and it’s fundamentally a catch-22 problem, but hopefully some of that points the way to doing it.

      • super insightful, thanks for taking the time to list out all the point! Loved the “bootstrapped” approach which I think is closest to what might be helpful for us at this stage. Thanks Jason!

      • Thanks man great article.

        haha it´s certainly “a catch-22 paradox”; I think that is the frustrating part because at the end -even at leadership. We have to learn it ourselves, become good at it, and then delegate it. or am I wrong?

  3. Love this philosophy. Every person you hire should be better than you. This is real growth. And as a leader it is the best fun you will ever have.

  4. Insightful article. Will be coming back for more.

    I love this thought: “Through delegation alone, if one person gets sick, a deadline is missed. Or if someone leaves the company, a strategy isn’t executed. With team-building, you have group knowledge. Someone being sick or leaving the company gets baked into the plan.” Wow. Well put. You know what you’re talking about.

  5. Speaking as a bootstrapper, I can offer a slight variation on this…

    When you are short on funds, you have to be selective about proven world-class people, because they are often expensive. For instance, someone better at me than marketing would demand at least $250,000 per year in cash compensation, not to mention stock. Not a dealbreaker necessarily, but I can only afford one or two of those people at a time.

    The alternative? Ask the question:

    Can this person push the company forward harder and faster than I can?

    Forget about experience or even skills. Spend a few hours with them and ask, “Am I dragging them forward, or are they dragging me forward?”

    People who are smart, creative, and driven just kind of have an accelerating effect on the conversation and the ideas. It’s almost like I can feel the company start moving faster when I’m around them. Every idea, every conversation is pushing something forward.

    Then there are other people who seem to make everything go slower. You have to explain things a dozen times, they want you to make decisions for them, they prefer pontificating on other people’s ideas instead of contributing their own.

    In my experience, you want to fill your company with the first group. And they are often inexpensive to grab. I just hired two for $36,000 per year each.

  6. Great points here Jason, I think your thesis in this article is spot on. Hiring the best and a focus on team building is a sure way to improve the organization one starts. However, what about “groupthink”? While rare, if groupthink occurs within an organization, it can cause the same limitations as relying on poor delegation. Therefore, what strategies can be implemented to limit the potential for groupthink within an organization? How do you actively cultivate the diversity needed to keep the organization as an in-group from stagnating?

    • Thanks Gene. There’s probably one “one rule” that kills groupthink — it’s a natural thing that any group, however motley, is likely to slide into.

      One help is focussing on outcome instead of “how,” and then actively encouraging brainstorming “how.” For example, if there’s only one suggestion for “how,” reject that condition and require there’s 2-3 ideas, thus causing people to think differently. The outcome is often fixed and maybe that’s OK, e.g. “lower costs” or “increase signups” or something are good for requirements and don’t represent groupthink.

  7. I really like the concept, and the reasoning behind it, presented in this article. Delegation is definitely not the most successful method to scale your start up. However, what kind of methods can one take to attract the best and brightest to an organization? Obviously, as you pointed out, to avoid simple delegation, one must seek out the best for each position not just an extension of one’s own abilities. But, if you are seeking individuals better than yourself in different aspects, how do you attract such individuals and assure them of the success they could bring to the organization?

    • Most jobs lack true empowerment. This means: Being given responsibility, and being held accountable, but then given the freedom to uphold those things.

      Top talent craves empowerment, otherwise you’re just a cog. The creativity and control is where all the excitement and fun is. Sure there must be accountability (you did what you said you’d do) and performance requirements (you achieved the outcomes the job requires), but great people are happy to have that challenge, so long as their entrusted with control in how it’s achieved.

      So, offer that empowerment. After all, you’re supposed to mean it!

  8. Hey Jason –

    Great post. I’m wondering how you feel about scaling with regards to finance. We have done an audit of our existing customers on and it struck me that many of them come to us in order to help manage the financial side of their growth. eg: avoiding rogue spending without getting in the way of letting people get their job done etc. After microconf I’ve been searching for a “position” we can take with the product other than just “purchase order software”. I’m trying to figure out if we can put some good content around how to manage finances when you start to grow fast (via sales or investment or whatever).

    Other than hiring good people, do you have any insight on how empower new hires financially? Is there advice you can offer on how to spend?


  9. The article definitely helps me develop my view of delegation and look at delegation as it relates to small business owners.

    hadn’t before thought about delegation as team-building. I used to get
    into the trap of delegating tasks, but the author is correct that that
    form of delegation only helps develop “a team that is not materially
    better than the founder, at anything. Which is incredibly limiting for
    the company.” As one of the commenters spoke towards, by simply
    delegating tasks or even projects to individuals who are only as good as
    the leader, then the organization stagnates. In contrast, when you
    “hire people who are better than you at every position,” your
    organization grows and moves forward.

    So then, the goal is not
    necessarily delegating, but team-building. And this requires letting go.
    I’m not necessarily sold on that it means letting go of ego and
    negative-pride. Are founders and entrepreneurs inherently egotistical and prideful? If I task-delegate, am I trying to be the hero? Do I think it’s all about me? Or did it have to be all about me and now I have to let go of the previous way of operating? Regardless, I do agree that team-building “means the team is trusted to own [goals], has obligations
    around [those goals], can figure out and execute all the details, and is
    responsible not just for meeting initial expectations, but increasing
    their expectations of themselves.”

    I was
    talking with my younger sister, and she was exclaiming that
    her current boss and administrative leaders “don’t know what they want!”
    and “their expectations aren’t clear!” I imagine this is happening in
    part because they may not have directly empowered her to be better than
    they are. She’s taken a great approach by creating her own expectations
    and increasing them as she moves forward, but I wonder if all the
    members of her team feel empowered to do the same – to be better at
    their jobs than the “boss” is.

    How is team-building responsibility shared and distributed? Is it employee to employer? Vice versa? Member to member?

    And if it is
    the leaders’ job assemble and manage a set a people who are all
    better-qualified than that leader to do those jobs, then are the
    leaders’ then expected to be the best at organizing and managing said
    team? Does leader = best team-builder and coach?

    is responsible for team-building, whether me-the-leader or
    me-the-member or me-the-member-leader, I want to surround myself with
    greatness, greatness defined as others who want to do the same, others
    who want to surround themselves with people who are better and more
    qualified than they are at their jobs. Thus, the organization grows,
    develops, and moves forward. YAY!

  10. Scaling by delegation is not good enough, so that’s why most entrepreneurs and businesses should invest more in virtual assistants to help with productivity and meet deadlines. has been doing this well for most project that needed completion within a certain time frame.

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  12. Fantastic read, and I feel it’s one I’ll have to keep coming back to every few months as I grow FullCast. These are the types or recommendations where most will nod their head, but few will actually implement. Specifically attributable to selfishness and ego which they will inevitably fail to let go of. Thanks Jason.

  13. Thanks for the article Jason. I think delegation is misinterpreted sometimes. You can empower staff by delegating responsibility and thus removing the ‘glass ceiling’

  14. Most of you think way to elementary. This is nothing more than a
    microcosm of a bigger problem. Please stop pigeon holing yourselfs into
    the rep/dem mantras

  15. Thanks for the ideas. It seems that there are only 2 types of situations considered in the article:
    1. Building teams by people hired by founders,
    2. Direct delegation where sicknesses etc. harm the result.
    But in case of “bootstrapping” companies can not grow that fast to implement first type even in 1 year. You can build a department of your core business (e.g. developers) from scratch but all other departments (sales, support etc.) at least firstly are represented by no more than 1 person.
    I have read the advice in the comment above for the “bootstrapping” case but the article itself does not give bootstrappers good options to develop. Thus another catch-22 situation :)
    And anyway there is a problem of trust. It is cool when you have institutional investors helping you form your team or HR with network in areas you are not savvy in. But mostly it is not the case. And if you have a goal to hire people better that yourself they are mostly unfamiliar to you.
    For this case the article (as I have understood it) suggest only 2 ways: either to delegate or to “build a team”. The latter case suggests to not micromanage, gain more free time by losing control over many aspects (an empowering your employees with that control).
    It is exactly what made Derek Sivers lose real control over his firm as he explained in his book “Anything you want”. He actually held the share but the management thought he was odd and wanted to relieve the company from him.
    Yes, it is also mentioned in the comment above that the art of managing that people is tough. But isn’t managing the company without corresponding expertise even more harmful that implementing delegation? Without that wisdom the article seems to be like a mini-skirt in that famous quote: reveals much but hides the most important.

  16. Fantastic read, and I feel it’s one I’ll have to keep coming back to every few months as I grow FullCast. and alsohere is all the info about jio products.

  17. Definitely an interesting article. My biggest concern, like many posters, is when you hire the “best of the best”. Certainly it makes sense to hire someone who’s skill set exceeds mine; this counteracts any foreseen limitations of my company’s service, but what happens when you hire someone that’s surely talented but headstrong, and conflicts arise? I feel like hiring the “best” isn’t just limited to the one with the most skills objectively but also the one who works with your team the best. It’s like adopting the best guard dogs to fight off robbers, but finding yourself unable to manage or command the dog yourself. I think, to some degree, if you’re CEO you still need to act as the “pack leader” even if you’re hiring people who are “better” than you in certain functions.

    • I was thinking more about this article earlier in the week and I feel like if I were a CEO I would struggle with finding a balance between acting as THE leader versus listening to my employees that I explicit hired because they were “better” than me at their jobs. What happens when you make tough calls as the CEO but your employees disagree? Easier said than done, I imagine.

      • Yup, that’s part of what makes being CEO so difficult. Sometimes the most critical decisions are the ones where you override. There’s no easy answer to it; that’s what the job is. The book “The Hard Thing About Hard Things” is one of the best descriptions of this in real life.

  18. Great ideas here. I agree that founders should be hiring people that know more than them for specific areas of the company or job. However, I’m not sure about hiring someone who thinks they know your idea better, or how to execute. As a business founder hopefully you are solving a problem that is passionate for you. Not everyone is going to share that same passion for solving the problem, but should be more competent than you in whatever area they are hired for. Your job is to make sure the business flourishes and your employees are happy, since it drives productivity. Hire the best and get the hell out of the way, because yes, you are bottlenecking.

  19. in todays world who doesnt delegate, lets be honest here. Teams are static, expire-able and have their talent constraints. Yes true if delegate you are the still the bottleneck, but if you can delegate like a rockstar, wheres the bottleneck traffic really?

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