Why is it so hard to delegate?

I recently attended another pitchfest where one of the smart-aleck, big shot, junior venture capital associates asked the entrepreneur a classic question.

“OK, good presentation, but how are you going to scale?”

There has probably been more than a zettabyte of advice written on that subject. It is a thorny question that does not necessarily lend itself to a logical playbook with bullet points, follow the bouncing ball.

One requirement, for sure, is to learn how to effectively delegate. As in give it up, let go, release the death grip. Trust your team.

Now this is definitely easier said than done. In my little AI startup, I serve as the CEO, but by now, the technical complexity of our product has left me in the dust. So I have to delegate. But to whom, and how much. And who is accountable.  

Our investors are patient, but only up to a certain point. Sure, delegate, trust the team, but don’t be naive. Every CEO knows the refrain wafting down the hall, who is minding the store, followed by “maybe we need a new leader.” 

For advice, I turned to Elsbeth Johnson, a senior lecturer at the MIT Sloan School of Management, who recently authored a research paper whose conclusion was that “leaders too often find themselves mired in the details of their teams, with debilitating consequences.”

She outlines four challenges in her paper. One is “decide what to delegate.”  This has some nuance. If you only give an assignment that is easy and obvious, sort of crossed fingers, one hand behind your back kind of thing, then a successful outcome gives you the personal productivity dopamine hit of “that felt good.” And you want to do that again. 

Don’t fall for the sugar high. The real requirement in this situation is to “set the context.” Johnson writes that “strategic initiatives were more likely to succeed when the leader set the desired outcome and left the execution decisions to the team.” In other words, explain the problem and then go to lunch.  

Activity-based work always feels better than context-setting work. Move the ball, easy to measure. Concrete action, obvious productivity. That’s why they are paying you the big bucks. Wrong. Don’t just do something, stand there.  Johnson calls that “reframing your focus.” Set longer-term goals and hand off responsibility. Let the junior members of the team shine. 

Again, easy to say. But in your startup, if you wake up, look around and realize all that delegating isn’t getting anything substantive done, then reframing is just another word for pack your bags and hit the bricks.

Johnson writes that another puzzle in scaling is to “establish accountability and support,” and set a schedule for reporting on the assignment. Benchmark against the competition, measure outcomes, not just effort.

 A small company needs frequency, as in what have you done for us lately. It’s due when it’s due. I like to channel Vito Corleone, who always insisted on hearing bad news at once.

Repeat context. “Why are we doing this?” My co-founder recently sent out an email reminding the 37 folks on this team what we agreed to deliver 30 days ago. No wandering, no project creep. Build the bridge as designed, don’t add a flower garden. 

But then top management has an equal responsibility. The org chart flows both ways. Don’t go randomly asking for some details in an area that is orthogonal to someone’s primary effort. Your report can’t know it all, nor should she. You want to know it all, go ask Turing.

Johnson says, “create a limited definition of work.” To scale is to delegate, and if that is the goal, then a leader’s real work is not just demonstrating personal excellence, rather it is learning how to expand the knowledge base of the organization. 

Not everyone has the personality or desire to delegate. Some leaders just like doing. If you are a famous spine surgeon, and you love slicing and dicing, then understand your limits and embrace your love. Let someone else train the hospital staff. In a law firm, don’t ask the rainmaker to train the associates.  

In my little AI company, I have completely delegated/outsourced the hard, grunt product technical scaling puzzle to my co-founders.  

I like to do deals.  After all, someone has to do that.

Rule No. 801:  Recognize your limits. 

Senturia is a serial entrepreneur who invests in startups. Please email ideas to neil@askturing.ai.