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  • Writer's pictureBenjamin

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Updated: Jan 28, 2023

Appointing a new leader for your growing startup is both exciting and daunting. You are adding someone who can have an exponential impact on driving and sustaining growth. At the same time, hiring leaders is scary as the team wonders about the expected changes.

Here are some considerations when making an executive hire:

  • Set expectations

  • Know what to seek

  • Find the right leaders

  • Move forward

  • Evaluate fit

Set Expectations

A new leader will have an outsized impact on the whole team. To make that experience positive, you want to manage expectations across the company, including those of candidates for the position, members of the leadership team, all employees, and other stakeholders like investors or clients.

Candidates. Talk about your business success and emphasize the growth plan, the expansion of opportunities, and company values and culture. As someone gets close to being hired, you want them to meet many team members. During these conversations, openly discuss concerns about their fit in the company and the challenges they may face. Initiating an open, constructive discussion helps to set the right expectations.

Leadership Team. Discuss the companyโ€™s expansion plan and where the executive will complement the existing leadership team. For your startup to grow, employees may need to specialize more. Openly discuss how this evolution might be uncomfortable for people who are used to handling many different tasks. Directly address concerns around responsibilities, teamwork, and culture.

Investors and Key Stakeholders. Explain your thinking around hiring for this role and get their opinion on the ideal backgrounds and characteristics. Be prepared to discuss their thoughts on the timing of the hireโ€”and if hiring other key personnel first makes more sense.

All Employees. Share your journey and plans, explaining how this new leadership position fits into your companyโ€™s evolution and how it will improve the business. If possible, convey how employeesโ€™ roles will be affected and what future opportunities might look like.

Know What to Seek

The leader should be bright, capable, and skilled, with a background across multiple companies. Hopefully, they've made mistakes and learned important lessons. Success is a weak educator.

There are many other characteristics to evaluate:

Connection to Vision and Values. You want someone who can advance the company and its process and systems while grounded in your culture and purpose.

Complementing Personalities. Based on your current strengths and weaknesses and those of the leadership team, determine what skills and styles will help the team dynamic.

Immediate Impact. Seek someone who can make significant, fast improvements (e.g., knowledge, management, or reputation).

โ€œThe most effective leaders score high

in both confidence AND humility.โ€

โ€“ Adam Grant

Self-Awareness. Confidence is knowing that failure is not trying. Humility is realizing there is always better but never best.

Effective Leadership. Will this person encourage productivity and cooperation both within their team and across the company?

Focus on the Mid-Term. You want them to be a strong fit for the position over at least the next twelve to eighteen months. Someone underqualified will never get traction, and someone overqualified may not be able to embrace the current role as they are used to a different environment, e.g., higher budgets and more direct reports.

Entrepreneurial Mindset. Identify someone who will treat the business as their own and work to take the company to the next level.

Non-Technical Skills. The company is still evolving, and you want someone flexible, creative, and motivated. They should demonstrate a balance between strategy and tacticsโ€”something worth confirming through references. You may also value their connections to people in the industry, potential clients or partners, and other useful resources.

Find the Right Leaders

Expect a long recruiting process. It will be challenging to find the right person to meet all of your criteria.

One way to get a better idea of how to find the right person is to interview three to five amazing people who currently have this role. You want to understand the best place to find applicants across all demographics, how to distinguish great candidates from good ones and the best way to screen people.

Rely on investors and key stakeholders to introduce current experts and recommend potential candidates. You may also ask other founders, especially those who are two steps ahead in the growth process and may have recently gone through a similar experience. Finally, ask your team, vendors, and reliable clients if they know of potential candidates. Your success is in their best interest, too.

As you end the hiring process, you may ask a notable investor or an impressive client to interview finalists to impress the candidate.

Iโ€™m biased here but consider the option of an interim or fractional leader who can show you how the role will function at lower cost and risk. A fractional leader provides a sense of what you will need for the full-time position. Their final project may be to help recruit their full-time replacement.

Move Forward

Once the new leader is decided, circle back to all stakeholdersโ€”the leadership team, employees, investors, and othersโ€”to inform them about the new leader. You want to be clear about the new leaderโ€™s role and anticipated impact. You should also promote their start on the website and across communication channels.

Explain what the new leader will do in the first few weeks, including their goals, duties, and onboarding plan. If you expect the new leader to make changes that the team will not like, explain the reasons behind their changes and openly address any concerns or hesitations. As the founder, you want to set up everyone for success by setting clear expectations with all stakeholders.

The new leader should participate in the regular onboarding process and have the opportunity to join other teamsโ€™ meetings, sales demonstrations, and client reviews to learn moreโ€”and to explain their position when appropriate.

Evaluate Fit

You may not know if someone will be a strong fit in their role for at least a couple of months. Here are some early questions to ask in evaluating someoneโ€™s fit:

  • Are they proactively describing an effective and realistic plan for the next year?

  • Have they met everyone on the team and learned their job functions, motivations, and career development plans?

  • Do they own their decisions? If the founder is still making team-level decisions after hiring a team leader, for instance, you need to uncover and address the issue.

  • Are employees going to them for help? If employees do not see them as a source of knowledge and support, that is a bad sign.

  • Are they balancing strategic plans and tactical actions? Someone weighted to one side may not make an impact in a startup.

Pro Tip: If someone is struggling, address and correct the problems immediately. Even experienced leaders could start slowly and would may benefit from guidance and support.

You may be tempted to believe they will solve any issues without you. While that resolution may happen on its own, a better approach is to ensure there is a plan to change and to give advice on how to navigate the company toward solutions.

If the new hire is not going to work out, decide to terminate them quickly. The larger impact of a leadership role can mean more damage if they remain struggling for a long time.

Key Takeaway: Hiring a new executive can be exciting and scary as people wonder about the expected changes. Set clear expectations for the leader and everyone impacted.


Scale: Reach Your Peak has over 130 independent topics across 500 pages including leadership, growth, sales, marketing, operations, finance, and teams. Each topic takes five minutes to gain invaluable insights, best practices, and practical options like this one.

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