Struggling With When to Hire, Manage, or Let Go as a Founder?

You're not alone.

As a coach for founders and CEOs, one of the most common questions I hear is: "How do I know if someone is right for my team—or if it's time to let them go?"

While these decisions often feel complex, the framework for making them can be straightforward. Let me share insights from two decades of building and advising high-performance teams.

Start with the End in Mind

Before evaluating someone, get crystal clear on what "right" looks like. Identify 4–7 non-negotiable characteristics someone needs to succeed in your organization.

But here's the crucial part–two of these must be:

1. 100% Investment in YOUR Vision This means they don't just understand your vision - they make it THEIR vision. When someone truly internalizes your vision, they become a force multiplier. Without this alignment, you'll face constant friction, even if everything else looks perfect on paper. I've seen countless partnerships fail, not because of competency issues, but because of misaligned visions. One founder I worked with brought on a highly skilled CTO who had different ideas about the company's direction. Despite the CTO's technical brilliance, the misalignment created constant tension that eventually fractured the entire tech team. Bonus for Founders on this point: this is also relevant to fundraising! Remember that with each investor, you give up some degree of control of your company. Therefore, you need to make sure that their vision is aligned with yours BEFORE you sign the term sheet.
2. Relevant Experience Unless you genuinely love teaching and managing (and have the time for it), hiring for experience is crucial. Yes, potential is valuable, but building a business is challenging enough without having to build your team's fundamental capabilities simultaneously.

Beyond these two core requirements, consider characteristics like:

• Work ethic
• Drama-free mindset
• Values alignment (e.g., honor above profit)
• Problem-solving ability
• Cultural fit
• Communication style
• Adaptability

The Art of Discovery

Here's where many founders miss the mark: they ask direct questions and get rehearsed answers. Instead, craft questions whose answers INFER the information you need.

• Don’t ask: "Are you hardworking?" Do ask: "Walk me through a typical day and week at your last job."
• Don’t ask: "Do you align with our vision?" Do ask: "What excites you most about where we’re heading? How do you see yourself contributing?"
• Don’t ask: "Are you good with conflict?" Do ask: "Tell me about a time you disagreed with your boss. How did you handle it?"

Making the Hard Calls on Hiring

Perfect candidates rarely exist - you're often dealing with tradeoffs. Maybe they have your two non-negotiables (vision alignment and experience) but only meet two of your other three core criteria. This is where thoughtful evaluation becomes crucial.

Ask yourself:

• Can this work, given our current team and resources?
• What support or systems would we need to put in place?
• Am I willing and able to provide what's needed?
• Does the upside outweigh the effort required?

Sometimes, a candidate who's an 80% fit but highly self-aware and eager to grow can be better than a 90% fit who's rigid or overconfident. Once you know it’s tradeoffs you’re evaluating, and not perfection, it’s much easier to come up with good decision criteria for your situation.

Evaluating Current Team Members

This requires a different approach. You're not re-interviewing them, but rather evaluating their current performance and alignment. Consider:

• Are they consistently demonstrating alignment with your vision through their actions and decisions?
• Is their experience translating into the results you need?
• How are they impacting team dynamics and company culture?
• Have you provided clear feedback and opportunity for improvement?

If they're struggling, use the 4 C’s Framework to uncover the root cause:

1. Competency Issues: Do they lack the skills or knowledge for their role? If so, do you have resources to train them or support their development?
2. Character Issues: Are there fundamental behavior patterns causing problems - like resistance to feedback, emotional volatility, or disregard for commitments? These are the hardest to change and usually require specialized leadership experience to address. Often a deal-breaker.
3. Communication Issues: Different styles (task vs. people-oriented, direct vs. processing) can create friction. These are typically adaptable through coaching or training, provided you have access to the right resources, and a team-member open to and committed to growing.
4. Commitment Issues: Look for patterns. If someone who was previously engaged suddenly changes, there's usually a specific cause that can be addressed. If they've never shown willingness to put in extra effort or take responsibility for their performance, it likely indicates misalignment with your vision - a fundamental deal-breaker.

Why It’s Crucial to Let Go When Needed

Remember, keeping someone who isn't right for your organization isn't kind to anyone - not to you, your team, or even that person. They could be thriving somewhere else that better matches their vision and capabilities.

Additionally, keeping someone who, after being given adequate feedback, appropriate management, and sufficient training, continues to underperform, sends a message to your whole company that that level of performance is acceptable. It’s not.

A Personal Note: I've made the mistake of holding onto people too long, hoping things would change. It never served anyone well. Yes, it’s always hard to lose someone, and emotionally, to let someone go. However, the sooner you make the hard call, the better for everyone involved.

Action Steps for Founders

1. Identify your 3–7 non-negotiable characteristics for team success.
2. Craft inference-based interview questions for each.
3. Review your current team using these criteria and assess their performance.
4. Schedule the necessary conversations—both the hard and encouraging ones.

??Final Thought

Remember, building a great team is one of your most important jobs as a founder. Do the hard things now; they pay enormous dividends later.

Question for You: What’s your most important non-negotiable characteristic when building your team? Share in the comments!

You got this!

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