By: Natalie Johnson
Companies invest heavily in executive coaching, yet too often measure its success with one question: Did the leader find it useful?
The sessions happen. The invoices are paid. But the questions that matter go unasked: What behavior changed? Who around the leader noticed? What business outcome improved?
David B. Frost, CEO of fassforward, believes “useful” is too low a bar. Coaching should create visible progress and measurable business value. Whether it does is often determined before the first session begins.
Frost challenges two common assumptions about coaching. First, it rarely works when imposed on a leader who does not want it. Second, even willing leaders make limited progress when coaching stays entirely between coach and client. The strongest engagements involve key stakeholders, define two or three clear areas of opportunity at the outset, and measure progress through changes others can see.
The Volunteer Problem
Frost puts consent ahead of methodology. “Executive coaching is most successful when the leader asks for it, rather than being told to do it,” he says. “Without that engagement, coaching becomes another meeting to get through and another box to check.” That sentence should trouble anyone running a talent function, because a meaningful share of coaching in large organizations is assigned rather than requested. It arrives attached to a performance conversation, a 360 result, or a promotion nobody was quite sure about. The leader shows up, participates politely, and the engagement produces exactly what compliance produces everywhere else, which is attendance.
The second condition is awareness, and Frost frames it as the real product rather than a preliminary step. “The best gift coaching can give a leader is a clearer understanding of their strengths and, more importantly, their challenges,” he says. “Once those challenges are brought into the light, the leader can recognize the behaviors connected to them and begin to change.” What follows is not dramatic. He is direct about the pace: coaching “doesn’t create a sea change overnight. It creates small, manageable behavioral changes that add up to meaningful growth over time.” Executives conditioned to expect quarterly results from every investment tend to misread that timeline as weakness. It is closer to the opposite. Behavior that shifts in a week tends to shift back in two.
Why Leaders Build Teams That Cannot Challenge Them
The most common blind spot Frost encounters is one leaders rarely diagnose in themselves. “The most consistent gap I see is leaders hiring people who think as they do,” he says. “I did it often during my career on Wall Street. It is how we are wired. We naturally gravitate toward people who think, act, and solve problems the way we do.” The admission matters more than the observation. This is not a failure of character or an oversight that better hiring discipline fixes. It is a default setting, and it compounds quietly, because each hire feels like a good one at the time.
The organizational cost shows up at the top. Using Thinking Patterns, fassforward’s foundational tool, Frost says the same cognitive styles frequently repeat across a leadership team, “leaving important perspectives missing.” A team assembled that way will reach consensus faster, but also be more likely to be unanimously wrong. Frost’s prescription is uncomfortable by design. “The hardest thing for a leader to do is surround themselves with people who think differently,” he says. “The best leaders surround themselves with challengers. These are people who see different risks, ask different questions, and offer perspectives the leader would not reach on their own.” Boards that worry about groupthink usually look for it in the deliberations. It gets built years earlier, in the hiring.
Measurement Belongs At The Start, Not The End
Here is where Frost takes his sharpest position. Coaching conducted entirely one-on-one, he argues, is structurally prone to confirming what the leader already believes. “The leader brings their version of events, the coach responds to that version, and the work can unintentionally reinforce behaviors and habits.” That is a pointed critique of the confidential dyad the profession has long treated as sacred. His alternative brings the sponsor, the HR business partner, peers, and direct reports into the process at the outset, where they help identify two or three development opportunities and stay engaged as the work continues. “That creates accountability for both the coach and the leader,” he says. “Progress is no longer based solely on how the leader feels. It is measured by whether the people around them can see a meaningful change in their behavior and impact.”
On return, Frost is blunt about sequencing. “We define ROI at the beginning of the engagement, not at the end.” Vague goals are the enemy. “Become more strategic” fails his test because nothing about it is observable. Delegating more effectively to free up time for growth priorities, accelerate decisions, or build capability across the team gives everyone something to watch. The engagement then returns to those areas at intervals, gathering real-time feedback rather than waiting for a closing report. “The question is not whether the leader has completed a goal,” Frost says. “It is whether their behavior has changed and whether that change is improving the performance of the business and the people around them.” Any organization that cannot answer that question about its own coaching spend is buying reassurance, not development. Frost expects AI to widen coaching access to first-time managers and individual contributors long before they reach the executive ranks, while human coaches carry the judgment and emotional understanding the hardest moments require. His framing of the split is the cleanest summary of where the field is going: “AI scales knowledge. Leadership scales judgment.”
Follow David B. Frost on LinkedIn for more insights on executive coaching, leadership development, and measurable coaching outcomes.
