A CEO of a tech startup approached me for coaching, citing tension with her co-founder, the CTO.

The CEO requested weekly coaching sessions to help her think through how she can better navigate the conflict between her and the CTO. She added that the CTO was unwilling to be coached, having told her that he “does not need coaching. [The CEO] just [needs] to learn how to listen.”

I suggested we start the project by interviewing the CTO to better understand his perspective.

During the interview, the CTO shared that he and the CEO disagreed on how to grow the company. With no resolution in sight, the CEO had volunteered to test the waters with the investors. If she could raise a series B round based on her strategy, that would be the end-of-story.

After a month or so of fundraising, the two had an update meeting. During the meeting, the CEO listed everyone to whom she had spoken about funding and what the conversations entailed. Unfortunately, all the CTO wanted to know was whether they were going to get funded. So after patiently awaiting his turn, he asked whether they were going to get funded. At that point, the CEO got irritated, which sparked an argument that ended with her storming out.

From the CTO’s perspective, the CEO was “too emotional for her role.” He believed it was time she was replaced with someone “more competent and even-keeled.” In fact, he had already delivered his statement of no confidence to her.

Based on the interview, I suggested the CTO meet with the CEO and I every month in addition to the weekly coaching sessions between the CEO and I. I also proposed that during the monthly meeting, the CTO say what he wishes to say to the CEO first. Then when and only when he’s certain the CEO had heard him, will the CEO get her turn to speak. The CTO and the CEO both agreed to this arrangement.

What became clear during the first few coaching sessions with the CEO is that the reason why she became irritated during the update meeting was twofold.

1. Lack of clarity with her business model.
   A slew of investors she had pitched, all rejected her outright, whereas one potential investor continued to meet with her trying to learn more about the company. She felt as if he was the only chance she had, and wanted to make sure she earned his approval. However, he had shared some skepticism around her business model without suggesting a solution. Lacking clarity on what to do, she needed help.
2. Feeling betrayed and unappreciated by the CTO.
   Unable to make progress with her business model, she felt helpless. Feeling as if she could not ask the CTO’s help, she felt isolated and frustrated, unable to receive help from someone she had relied on for many years. She also felt as if the CTO was taking the fundraising effort for granted, “sitting around waiting for [the CEO] to bring home the bacon.”

Based on these insights,

1. I made sure that subsequent monthly meetings among us three not only focused on navigating difficult conversations, but also allowed room for the CEO and the CTO to provide emotional support for each other by explicitly expressing genuine appreciation for one another in far greater detail than they were used to.
2. I also invited the CEO to shift the focus of our weekly coaching sessions to redesigning her communication approach with the potential investor. The CEO said she felt relieved to receive and accept this invitation.

Over the next few coaching sessions, the CEO acquired three key insights for her development.

1. From the investor’s perspective, her pitch was difficult to understand and empathize.
2. The strategy offered short-term solutions based on customer feedback, without demonstrating a more in-depth understanding of the customers’ latent needs that could be fulfilled for longer-term growth.

3. There was a hole in the business model that only became clear once the above two issues were addressed.

During our weekly coaching session, the CEO confessed to feeling regret for having focused on building the company during her daughter’s childhood. She also felt she hadn’t spent enough leisure time with her daughter recently. Several months of grueling work on fundraising and her conflict with the CTO had led her to ask herself if “all this was worth it.” I intuited this to be a symptom. So I invited her to go deeper and we discovered that her regret was significantly influenced by her relational tension with her mother.

It turns out, the CEO grew up with a mother who also prioritized work over spending time with her daughter, the CEO. However, the CEO had promised herself to not be “that ungrateful daughter” who resents her parents for not having spent time with them. So she spent much of her adult life forgiving and reconciling with her mother. However, in recent years, her mother had become highly critical of the CEO for spending so much time at work. In particular, her mother had accused her of being “selfish.”

Based on these insights, subsequent coaching sessions with the CEO were primarily focused on 2 challenges.

1. Exploring her relationship with and experience of her mother.
   Having spent much of her adult life forgiving and reconciling with her mother, it was painful to see that very mother turn around and accuse her of being selfish. However, she had been repressing this pain, because she felt as if “letting [herself] feel the pain would break [her].”
2. Learning to delegate more effectively.
   The CEO acquired key insights from her daughter that it was less that the daughter wished to spend more time together on leisure activities, and more that the leisure activities they already engage together be qualitatively better. The CEO also learned that the quality of their leisure activities can be improved if they were less interrupted by work calls and if she were less anxious about something going wrong at work. This required delegation, but her past efforts to delegate had been ineffective. So she had to redesign her approach to delegation and let her team regain her trust.

Due to a relational tension between the potential investor and the existing shareholders, series B funding eventually fell through. Fortunately, the CEO was no longer wedded to raising a series B round as she admitted that the purpose of the round was primarily to prove the CTO wrong.

The CTO was now also on board with the CEO’s strategy as he could see the positive potential of the new business model whose hole had been patched. Since the relational tension between the CTO and the CEO had lowered, they agreed to work together to revise the strategy to grow the business without more investment.

Such a change in strategy combined with the redesign of the CEO’s approach to delegation, the CEO now wanted to focus our engagement on improving the effectiveness of her delegations and innovating the organizational structure required to support the new strategy.

This marked the start of a retainer project coaching her on her ongoing efforts to design a organizational structure required to support the new strategy.

A CEO of a multinational consumer goods startup approached me for coaching, citing

1. Tension among his 7 direct reports across two branch offices in countries A and B.
2. A general lack of proactiveness or a sense of ownership in the direct reports’ performance.

During the interview, direct reports from both country A and B shared their significant distrust for one another. This was to be expected. However, several unexpected insights into the influence of the CEO were also discovered.

1. The Impact of the CEO’s Venting.
   More than one of the direct reports backed up their distrust by saying “even the CEO doesn’t trust them.” It turns out, the CEO often vented his frustration regarding his direct reports in country B to his direct reports in country A. The CEO was born in country A and his venting involved stereotypical accusations of the entire ethnic group of country B as lazy and untrustworthy. This, in turn, amplified the stereotypes that his direct reports in country A already had against those in country B. Given this, it was only a matter of time before the direct reports in country A had significant trouble giving their peers in country B the benefit of the doubt.
2. The Impact of the CEO’s zeal for “self-management.”
   All of the CEO’s direct reports professed to feel anxiety and overwhelm in their relationship with the CEO. According to them, the CEO was a proponent of “self-management” and wanted people to “learn by jumping in and figuring it out.” While the absence of micro-management was appreciated, they felt this was merely a different kind of torture. For example, when they saught the CEO’s guidance, he often asked them to “do whatever [they] want and go crazy.” However, when they did whatever they wanted and went crazy, he often criticized them for having no basis in logic. In cases where the CEO did approve, he asked for so many revisions that the direct reports’ sense of ownership diminished with each successive revision. As the vicious cycle ensued, it was a matter of time before the direct reports had lost all motivation to be proactively engaged.

I delivered these key insights to the CEO and suggested he put a stop to both his venting to his direct reports and his penchant for “self-management.” I also suggested he and his direct reports work with me every month to engage in difficult conversations to build trust. The CEO also requested I work with him 1-on-1 on a biweekly basis to help him learn how to grow his direct reports through mentorship instead of self-management.

In addition to our biweekly coaching sessions, I asked the CEO to share his energy level with me every weekday along with a brief description of what is draining him. Over 3 months, I observed that his energy level dropped most significantly when he felt tension mentoring his direct reports.

When I shared this observation with the CEO, he said he found mentoring to be too slow and frustrating, adding that “[the direct reports] don’t know how to be grateful.” I intuited this to be a symptom. So I invited him to go deeper and we discovered that his frustration was significantly influenced by his relational tension with his family.

It turns out, the CEO had been adopted as a child into a family that treated him like a servant to their other children. While he was now estranged from his stepfamily, he remembered growing up being told that he is different and that as the youngest he must look after his three older brothers. Given how much time and energy he had to dedicate to his brothers, he felt he never had the autonomy to do what he wanted.

Throughout his teens, he also suffered a chronic physical condition, which required regular checkups and frequent injections that caused great pain. However, his step parents had told him to go to the hospital alone because his step brothers needed their attention more. As a result, he had internalized the importance of repressing pain, frequently reciting to himself that “crying does not solve problems.” One of his most vivid childhood memories involved getting hospitalized on his birthday, wishing that his step brothers would visit to throw him a birthday celebration like the ones they had. Nobody came.

Based on these insights, subsequent coaching sessions with the CEO were primarily focused on 2 challenges.

1. 1. Discerning between his past self and his team.
      From the CEO’s perspective, he was exercising compassion when he let his direct reports “self-manage.” The same was true of his efforts to be hands-on with their growth. After all, he was never given such autonomy or attention for his personal growth as a child. So he felt compelled to give it to others, claiming “they shouldn’t have to go through what I went through.” While both endeavors were well-intended, he acquired the key insight that he was also prone to confusing the needs of his past self with that of his direct reports.
   2. Designing a system of mutual support for growth.
      To realize the CEO’s intention to help his direct reports’ growth, he had to first persuasively communicate why he wants his direct reports to grow. Willing direct reports could then come up with their way of fulfilling that “why.” The CEO also had to receive feedback from the direct reports on how best he could support their growth. Without such clarity, it was likely that he would merely interfere despite good intentions.

1. How they could fulfill the CEO’s “why.”
2. What form of support from the CEO and their peers would most support their growth.

All except one of the direct reports accepted the offer. The one who refused soon quit, citing irreconcilable differences in values. The CEO took the opportunity to restructure his company so he can have only 6 direct reports.

With a plan in place around both what each direct report will do to fulfill the CEO’s “why” and how the CEO and their peers would support one another to achieve this goal, a social contract was put in place to follow up every month to ensure that they were on track. Any necessary course-corrections were also made during the follow-up.

A retainer project was spawned to coach the CEO through the carrying out of the social contract as well as making ongoing revisions whenever unforeseen challenges arise.