One idea in The Founder’s Dilemmas kept bothering me.
As companies grow, roles may need to be upgraded because the people who were right for the early version of the company may not be right for the next version. upgraded.
And I guess that makes sense.
A five-person startup and a 500-person company probably need different things from their employees.
But I kept getting stuck on the word upgrade.
Because why are we upgrading the role?
Why not upgrade the person?
Your Early Diamonds
Instead of:
“Do we need someone more experienced?”
Let’s ask:
“How can we develop someone we already have into what we need?”
And in reality, sometimes the answer is no.
There are situations where a company genuinely needs experience it doesn’t currently have. Hiring someone with a specific skill set can make perfect sense.
But replacing someone should probably not be the first development strategy.
Especially when the alternative is developing early employees.
These are people who took a chance on the company before there was much to guarantee that it would work.
They’ve already demonstrated something that is pretty difficult to manufacture later:
They care.
They know the company.
They know the customers.
They know why the thing exists.
And they have probably figured out how to survive a fair amount of chaos.
That stuff doesn’t exactly come with a job title.
Make the Next Stage Visible
You’re thinking about the future.
Forecasts, phases, expansions.
Thinking about the future of your early employees isn’t isolated from these things.
You know the volume you’re forecasting, you know the strategy for the next phase, you know where you are looking to expand.
You will need skilled people for all of these.
If you can take a moment to think about those skills, you can save yourself a lot of hiring stress later by informing your current, early employees of how you expect the needs to change.
That gives them a chance.
If a founder knows the company will need a department leader in two years, why wait two years to decide whether someone is capable of being that leader?
Tell them.
“This is where we’re going. This is what we’re going to need. Do you want to become the person who can do it?”
Now the employee has something to work toward instead of being surprised when the company suddenly decides their current skill set isn’t enough.
That also gives the founder useful information. Maybe the employee doesn’t want that role. Maybe they do, but need development. Maybe they are already taking steps toward it.
Either way, the conversation is happening before the replacement decision.
Growth Requires Cultivation
Startups are very good at creating pressure.
They’re not always as good at creating development.
Throwing someone into a growing company and giving them increasingly difficult problems can teach them a lot. But eventually, “figure it out” stops being a development strategy.
People need mentorship.
They need feedback.
They need opportunities to lead projects before they’re expected to lead departments.
They need to sit in on decisions that are slightly above their current level and understand how those decisions get made.
If we expect people to become more capable, we have to give them opportunities to practice being more capable.
Otherwise, we are judging them on a skill they were never given the chance to build.
Upgrade the Person First
I don’t think this means founders should never hire someone more experienced.
Sometimes the company genuinely needs a different level of expertise. Sometimes an employee doesn’t want the next role. Sometimes development isn’t enough to close the gap.
But I don’t think “this role has outgrown this person” should automatically be the end of the conversation.
There is another option:
What would it take to help this person grow into the role?
First, transparency. What will the need be?
Then, mentorship. How is my progress?
And let them demonstrate, give them stretch assignments. More responsibility.
Time. Space. Nurturing. And a little bit of proactivity.
We spend a lot of time asking whether people can grow with the company.
I think founders should also ask whether the company is helping them grow.
The early employee who becomes the leader the company needs might be a better outcome than constantly replacing people every time the company reaches a new stage.
The early employees have been helping to build our dreams.
Scaling, it’s our turn to return the favor.
Before upgrading the role, try upgrading the person.
References:
Edmondson, A. C. (2018). The fearless organization: Creating psychological safety in the workplace for learning, innovation, and growth. Wiley.
Wasserman, N. (2013). The Founder’s Dilemma: Anticipating and avoiding the pitfalls that can sink a startup. Princeton University Press.
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