Founder Friday: How Startups Can Navigate Losing Key Team Members

No one company likes to lose key team members, but it can significantly hurt startups that don’t have the layers in place or succession plans in place to handle the loss of cornerstone employees easily. What should your startup do if you find yourself in this unfortunate situation?

Identify Your Stars

You probably already have a pretty good idea of who they are, but don’t rely on your “gut” alone. Have a methodology that you use to validate those feelings. Your method should include both quantitative and qualitative components. Standardizing how you measure a team member’s impact will also help to remove bias.

Knowledge is Power

Now that you know your stars, focus on documentation surrounding their duties and processes…

  • A list of projects, statuses, and overall responsibilities
  • What processes do they follow?
  • What systems/tools do they use?
  • Who has the credentials to get into the needed systems/tools?
  • What are the responsibilities of their team (who does what)?
  • What are the most critical deliverables?
  • What external relationships do they own?

Knowledge transfer cannot occur without documentation. Things will get lost if you wait until someone is working a notice.

Who’s still on the bus, and what can they do?

Another pre-loss step is understanding who you will still have on the team and their capabilities. Maybe you have a single person on the team ready to be promoted, or the job duties can be split/shared among multiple team members. Either way, know what you have internally to understand what you might need from external resources. 

Those two steps help minimize the loss’s impact, but let’s fast forward to what you do once you know someone is leaving your startup.

Understand the Why

When you’re a founder, it is easy to take things personally. Whether it’s the unrealistic desire, some founders have that every team member should care as much as they do or how personal it feels when someone says, “I quit.” However, when someone you hold in high regard gives their notice, it is a fantastic opportunity to learn and grow. Let your guard down and understand why they are moving on. Have a structured exit interview. It’s an amazing growth opportunity.

Do You Counter?

We could take the standard recruiting firm approach pointing out that roughly 85% of counters result in the employee moving on within the following year. But we’ve also seen instances where counters have worked out. What’s been the difference between successful counters? Outside of money, there has been a shared commitment to addressing the other issues that led the employee to explore other opportunities. If you cannot or will not change, the employee almost always leaves.

Speak to Team Members Impacted Directly

Don’t let this turn into a situation where you are now losing multiple team members. Speak with them, get their insights, and make them part of planning how you intend to move forward. You want buy-in for the next move you make; that’s more easily accomplished when you listen to and address the team members’ concerns still there.

Don’t Forget External Stakeholders

You’ve already lost a key team member, don’t also lose clients and essential relationships that they owned. Just as you updated the team internally, understand that your messaging around the plan to move forward and the impact that will have on those external relationships is critical to maintaining them.

Change What Is Broken

There’s the quote, “insanity is doing the same thing over and over again and expecting different results” (misattributed to Albert Einstein). Between the exit interview and your conversations with the remaining team members, you should have an idea of some of what’s broken. Don’t repeat the same mistakes in the future; take action to plug those holes.


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