The Biggest Mistake I See Entrepreneurs Make

By Laura Gallaher, PhD, LHEP™

Summary Points:

  • Entrepreneurs often underestimate the coordination required to move groups of people in the same direction.
  • Leaders mistake clear expectations for micro-managing.
  • Leaders mistakenly believe that ambiguity creates agility

Read time: 4-5 mins

How Growing A Business Is Like Throwing A Dinner Party

I have spent the last 4-5 years working with growing companies, typically working directly with the founders as their idea becomes a start-up and grows into something bigger.

The biggest struggle I see entrepreneurs grapple with as they grow their companies is effectively transitioning from individual contributor to leader. In the beginning, the founder (or founders) is doing everything, wearing multiple hats, and when they have the good fortune to grow, they start to take some of those hats off….or at least they intend to.

The Dinner Party Metaphor

One of the metaphors I use for people is to ask them if they were going to have dinner all by themselves tomorrow night, how much would they plan that out? Most people say “not at all”, or occasionally they say they might think about it for 2 minutes to decide if they will eat in or out and if they need to go to the grocery store.

Now I ask, if you were going to have dinner with another person tomorrow night, how much would you plan that out? Now, it is a little more… definitely need to plan a time and location… and we’re now thinking not only of our own preferences but factoring in the other person’s as well.

dinner party

Next I ask, what if you were meeting 10 people for dinner? How much would you need to plan that out? At this point, there is a decent amount of work that must go into it….Coordinating the schedules of 10 people, or at least clearly communicating to all 10 of them the exact plan – time and location. In some cases, making a reservation or at least calling ahead will be critical to maximizing your evening – you don’t want to have a big herd of people hanging out in the lobby of a restaurant forever while the host waits for 2 tables near each other to clear out simultaneously to push them together to sit everybody.

And in extreme cases, sometimes restaurants even put together a specific menu just for your party, so any dietary restrictions need to be factored in. Now…you can bring 10 people together without factoring in their preferences and without doing a lot of planning, but you will likely enjoy the evening much less, and what could be an enjoyable 2-hour event could turn into a 3-4 hour “situation” that leaves people grumbling.

How the Metaphor Relates to Organizations

So… an organization can absolutely take the same approach. Leaders can make the time to get clear about where they are going, what their people prefer, and make sure everybody has received clear communication about the destination and the plan. Think back to the restaurant example again for a moment….wouldn’t an evening in a new location be that much easier if people communicated to you the best options for parking, for example? If they took the time to point out landmarks that you will see as you walk from a parking garage to the restaurant? Everybody would be much more likely to show up on time in the right location.

Therefore, as leaders grow their organizations, it becomes that much more critical that they are clear about their future destination, how they are going to get there, and what each person needs to do to make it happen.

There are 2 primary reasons why leaders typically fail to do this.

1) They believe being clear about expectations is micro-managing.
2) They fear that having a clear picture of the future means they can’t be agile and pivot as the market changes. Let’s break these down…

1 – Mistaking clear expectations for micro-managing

Be honest with yourself for a moment….when you have an idea in your mind about a task, project, or work you want to begin – when working for yourself and by yourself, how often do you begin without making the time to think through the path you want to take? You likely start down a particular path, and maybe realize partway through that you want to tweak or modify it in this way or that. You are working for yourself, so you can continuously work and shape your efforts as you go.

Once you delegate, without a crystal ball, your employees can’t predict exactly what you want. As much as we wish they could, they can’t always read minds. And here’s the kicker – even if they could read minds, maybe your mind is still a bit chaotic about what this project would even be!

Don’t make the mistake of sending your employees off to work without thinking through with them some of the basic parameters of an effort. Most importantly, make sure you are always clear about exactly what problem you are asking them to solve, and what will be different (from a results perspective) when the problem is solved. If you make the mistake of failing to provide clear expectations, your employees will likely disappoint you, and then in frustration, you may become this uber-micro-manager, annoy the crap out of everybody, and drive away your top performers. Roll up your sleeves, get in there, and help them get clear about the problem they are working to solve. Make sure they are headed in a good direction before you let them loose.



2 – Fearing that a clear future vision inhibits organizational agility

If anything, the clearer you are about your future vision, the easier it will be for your organization to pivot when the market shifts. Specifically, it will be easier for you to identify what changes in the market mean for the future you have outlined and your plan to get there. If we barely know where we are going, then we certainly don’t know what to change when it feels like a change is warranted!

The Destination Metaphor

Imagine I say to you… “Let’s meet up in Chicago in July. See you there!” – First of all, what are the chances that you and I will actually find each other in Chicago in July? Secondly, now let’s say we find out there is a massive convention (not for us) in Chicago in July – and we want to know how this affects our plans. Well….if we don’t know exactly when or exactly where in Chicago we are planning to meet, it is really difficult for us to know if this convention changes things for us (like making flights more expensive or hotel rooms selling out).

destination metaphor

Do the hard thinking proactively – make the time to get clear about your future vision, and get everybody marching in the same direction. Now, when your organization will inevitably need to pivot and shift direction, communicate one clear message to everybody to orchestrate that turn.


The benefits of planning and visioning are about all of the thought and conversation that go into creating the plan. When there is a shared understanding of why we are planning to do what we are planning to do, we are so much more prepared to manage external changes. When things change, we already know what we need to address because we have made the plan. One thing that helps me is to call the “Plan” the “plan from which we will deviate.” And then deviate with intention.

Also published on Medium.