Sticky Situations: The Leadership Crisis

This issue's "Sticky Situation" responses were written by Suzi Pomerantz, MT, MCC, Victoria Trabosh, CDC®, CEC, and Craig Carr, BCC, PCC, CPCC, and originally appeared in choice, the magazine of professional coaching. Click here to receive a FREE digital issue.

The Situation

My corporate client is facing a crisis in leadership. The founder/ CEO is an exalted, legendary character (think Steve Jobs), who could sell the company for millions and walk away. He built the company and the community around it, so I think he’s inclined to find a way to transfer ownership.

How can I help him decide, and if he stays involved, how can I help him find new leaders?

The Experts Weigh In

by Suzi Pomerantz, MT, MCC

As the coach, you have two distinct explorations to lead with your client on the subject of legacy:

1. What does he want his legacy to be as the founding leader of the company
2. What’s best for the organization?

As you explore the first topic, it’s worth asking him:

• What matters most to you?
• Why did you create the company in the first place?
• What is your highest purpose?
• What gives you meaning/ what do you find most meaningful about your contribution to the company?
• How would you like to be remembered?
• Who do you want to be in the matter of your transition out of the company you built?
• If you could go out in the best possible way, what would that look like?
• What, if anything, stands in the way of that exit strategy?

As you help him explore the impact to his organization:

• What is the core secret to the company’s success and how can you ensure that core sustains after you leave?
• What will be the community, leadership, and culture impacts to the organization when you leave?
• What approach would represent the most seamless and aligned transfer of power and cause the least disruption to the formula for success?
• Would intentional, strategic disruption create positive growth and innovation, and if so, how should you time your sale of the company in order to capitalize on that disruption?
• Are there potential home-grown leaders within the existing ranks of the company who could be successors?
• What are the ideal leadership characteristics, skills, and knowledge needed for the next generation of leaders?
• What can you do now to groom up-and-coming leaders and create a solid succession plan?
• What do you foresee to be the biggest challenge to the organization, culture, community, and employees?

Once he has some clarity about the above explorations, you might help him craft a communication strategy to his directs, the entire staff, the board, and the media, ensuring he controls the narrative of his legacy before, during and after the sale of the company.

He needs you to help him to remember who he wants to be and how to align his decisions and choices about legacy and succession planning and transfer of ownership in ways that are congruent with who he wants to be.

by Victoria Trabosh, CDC®, CEC

As a coach, your task is to help this leader surrender to the process of decision-making. In Chapter 12 of his book, Elegant Leadership: Simple Strategies, Remarkable Results (2001), Andrew Neitlich discusses how elegant leaders move things forward in such a way that others barely notice. They do this by building a foundation grounded by their vision and their commitment to get results.

As the coach, before assisting your client in creating a clear strategy to achieve results, work with him to commit to a plan for exiting the company or staying and growing the company. If he vacillates, he creates chaos for the leaders around him, his employees, and within himself.

You’ve described him as a “Steve Jobs” archetype. There are great lessons to learn from any leader, both positive and negative. Six traits outlined in the AboutLeaders.com website article by Joseph Carey (2017) about Steve Jobs:

• Have a Vision
• Develop the Passion
• Challenge the Limits of Your Employees
• Follow Excellence, Not Money
• Don’t Aim Below Perfection
• Take Risks

One way to help leaders is to assess their strongest traits. Then dive deep with the leader to explore how he or she will use their traits for strength, and not overuse them to create weakness, discourse, or chaos. Without space here to go through each of the six items above, as a coach, you know how each of these strengths can become a negative trait.

If you are good at speaking truth to power, the most significant advantage in your role as a coach is to have a serious discussion around the traits your leader exhibits, have the leader make a definitive decision on whether he will stay or go, and then craft a plan to carry out his vision. Will he allow you to hold him accountable? If so, get specific on what areas, and how.

One last point. Regardless of whether he stays or goes, he must create leaders around him. In this case, Steve Jobs would be a good case study for you to explore. Find out what Jobs did well, lessons learned from what didn’t work, and replicate and duplicate what fits while adding your client’s specific traits. Help your client build on his strengths so he can become a better leader through your coaching.

by Craig Carr, BCC, PCC, CPCC

You’ve done an excellent job distilling the situation to two issues where coaching has a place. The first is the CEO’s near-future, personal and purpose-driven choice about what to do with the company. The second is how ownership and leadership will transfer if he stays involved but not active. The question to you is:

“Do you want to do one of these, or are you ready for both?” 

As you engage the CEO, remember there is a personality difference between founders/builders of companies who are in love with their creations and those who want to grow a business, sell or liquidate it, and move on. 

Steve Jobs could have ridden into the sunset in 1985 with saddlebags of cash, never to be heard from again. He didn’t, of course, because his vision and mission were far more important to him than his desire to retire. 

If your inclination is that the CEO wants the company to continue, there are multiple options to consider. 

Does he believe a buyout or merger will help or hurt the people who loyally built the company with him? Raise questions and color in possible futures. Listen carefully to cues and body signals that reveal what he truly wants. Acknowledge all emotions that arise and bravely name them. 

It’s common for CEOs to think that if they stay involved, they can protect their people and products. That’s possible if they’ve negotiated that kind of leverage, which is rare. In other words, make sure he doesn’t delude himself into thinking that when the big dogs come to town, he’ll still be an influential player. 

Perhaps the best way for him to stay involved and score a cash payday is to offer ownership of the company to the employees (ESOP). It’s complicated but can be worth it in terms of protecting his legacy. Read up on this option so you can help sort the dynamics that are within the scope of coaching. 

Some of the most fun coaching you’ll ever do is the leadership succession of a company icon. It’s loaded and busy territory, and a coach perspective will make a huge difference. 

If it comes to pass, I recommend you advocate and get involved with the selection and seating of a succession committee and work closely with it to identify leaders who can fill those enormous shoes.

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Are you grappling with a sticky situation? You don’t have to go it alone. Let our senior coaches give you some different perspectives to consider. Email your situation to [email protected] and put “sticky situations” in the subject line. Let’s see what the experts have to say!

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