Coaching can have an outsized impact on CEOs and leaders in growing startups.
The challenge is understanding what kind of coaching you need because startup leadership coaching is hard to do well and different from traditional executive coaching. Before explaining what makes startup executive coaching unique and what that means for you, let’s define coaching.
In the startup community, “coaching” is a term that gets bantered around without a clear definition. Broadly, you’ll find four approaches.
First, you’ll run across charlatans who claim they have a “proprietary system to 10x your business.” Run the other way. This isn’t coaching.
Second, you’ll find mentors and advisors who refer to themselves as “coaches.” Advisors provide advice about what you should do based on their lived professional experiences. When their experience is directly relevant to your work, their advice can be very valuable. All CEOs should cultivate a network of mentors and advisors, but advising is different from coaching.
This leaves us with two coaching styles relevant to startup CEOs and executives. These two coaching styles mirror two different types of challenges and the various approaches to learning that come with them.
The first type of challenge is technical (and by this, I do not mean technological). Technical challenges are ones that experts understand well. These challenges are addressed by technical learning, which involves acquiring already well-established and defined knowledge. As a result, it’s the information that experts readily teach.
The second type is complex challenges without clear technical solutions. Learning to address these challenges demands deeper change, substantive adaptation, and often experimentation to achieve insight. This type of learning is required in two circumstances. First, it arises when a leader has the technical knowledge but can’t consistently realize the behavioral changes that would put that knowledge into practice. Second, it comes into play when the leadership challenge has no simple answers or off-the-shelf frameworks that will work.
A specific example will illustrate the difference between technical and adaptive learning. Giving critical feedback is a technical leadership skill. It’s an essential skill for startup executives, and several specific techniques will make any leader more effective. (Thanks for the Feedback is a fantastic primer.)
However, after learning these feedback techniques, many leaders still fail to apply them. This is an adaptive challenge. Sometimes, to use a new technique, a leader needs to make a more profound transformation and overcome internal and external obstacles that make it difficult to change how they behave in the real world. This type of change is adaptive.
Coaches who focus on technical learning use an instructional approach. They teach generally applicable and well-established leadership skills, techniques, and frameworks. This is sometimes called “performance” coaching, but I like to call it technical coaching.
Coaches who work with leaders on adaptive learning and change use a different approach based on active inquiry, collaborative problem-solving, and guided self-discovery. These coaches use a range of proven methodologies that help you create change and develop solutions to the adaptive challenges you face. This approach is sometimes called “developmental” coaching, but I like to call it adaptive coaching.
In established companies, executive coaching starts with the expectation that leaders know how to lead technically, but they need support actually realizing the changes in their behavior to realize their vision of themselves as leaders. As a result, most executive coaches focus on adaptive learning challenges. This type of coaching is certified by organizations like the International Coaching Federation (ICF), which defines “coaching” as purely adaptive (in the sense I’m using the term here).
The Unique Startup Challenges
Executives and CEOs in startups and high-growth companies face very different challenges than leaders in established companies.
Established companies spend decades training and developing leaders to prepare them for C-level responsibilities. High-growth startups throw inexperienced leaders into the middle of the battlefield and expect them to be expert generals.
As a result, startup leaders usually need to do both technical and adaptive learning to keep up with the growth of their companies. At the same time, they need to cope with a wide range of adaptive challenges in an environment that is rapidly changing, volatile, uncertain, complex, and ambiguous. Moreover, they need to do all of this fast.
In a fast-growing company, you probably need to learn skills you were never taught because your company is outgrowing your leadership experience. This demands technical coaching. A 1:1 teacher is impactful, given the speed you need to move and the value of personalizing the training to your current needs. This kind of teaching requires skill and real-world experience.
At the same time, if you’re like most humans, you’ll find that some technical skills simply don’t stick, and transforming yourself into the leader your company needs requires adaptive learning and coaching. On top of that, as a startup leader, you’re likely creating a new category or disrupting an existing one and trying to change not just what the business does but also how business is done, so you’re facing difficult adaptive challenges.
The Best of Both Worlds
As a result of these conditions, the best startup coaches excel at both technical and adaptive coaching. This combination is tricky to do well.
Adaptive coaching works best when the coachee is willing to be vulnerable, so it’s usually built on the premise that the coach and coachee are partners who play different roles without any hierarchy. Technical coaching is more like teaching. As a result, it may create a power dynamic between coach and coachee that can result in the coachee being more performative (striving for an A+ grade) — less vulnerable and willing to dig deep into the real issues that may be blocking their growth.
Despite the challenges, it’s possible to combine these two coaching methods. It requires higher levels of self-awareness for the coach and the coachee. Different coaches will handle this in different ways. Some lean harder into technical learning, others into adaptive learning. Regardless of their focus, savvy coaches are explicit about their role at any given moment in a conversation, so there is transparency and understanding. They skillfully adjust to your needs over time.
Another approach some coaches take is to leverage tools (articles, videos, etc.) to move some of the technical learning out of the coaching sessions so they can use the sessions for more adaptive learning — helping the leader translate what they’ve learned into consistent action.
Understanding the differences between technical and adaptive coaching and the need to combine these two practices is central to finding the right coach for you and your team.
Coaching was critical to my growth as a leader, and my experience working with great coaches inspired me to become a coach myself. I’d love to hear about your experience with coaching. Please comment with your thoughts and perspectives on the different styles of coaching you’ve seen and their impact on your leadership.
A Note on Terminology
While it’s generally accepted that there are different coaching styles, there is no consistent terminology. I’m proposing the terms “adaptive coaching” and “technical coaching,” but these terms are not yet widely used. You might hear “soft” vs. “hard” coaching or “inquiry-based” vs. “instructional” or “coaching” vs. “training.” You also might come across “developmental” vs. “performance” coaching. Many coaches won’t mention the differences, so you’ll need to determine how they approach their work. Regardless of the terminology, the themes and general conclusions above hold.
I came to these two terms as I sought to understand why there were two distinctly different coaching styles in the startup world and why both were successful in the right context. This framing is based on the differences between adaptive and technical challenges developed by Ronald Heifetz and Marty Linsky (See Adaptive Leadership). In addition, Keith Naber, VP of Professional Programs at the Hudson Coaching Institute, suggested to me that Heifetz’s framework could be applied to different modes of learning and coaching. The content above is my own perspective derived from these insights.
Note: Confidentiality and respect for privacy are paramount in my coaching practice. The insights and advice shared in this post are based on my general experiences and knowledge and do not represent the situation of any specific individual or company.