Jonathan Basker, CEO & Founder of Basker & Co. - Leadership with a Proactive Lense

Jonathan Basker, founder of Basker and Co., has spent his career studying how humans operate inside early stage companies. His past roles span Etsy, BarkBox, Handy, InVision, and betaworks, where he developed one of the original models for venture studios. The conversation focused on what proactive leadership looks like in companies that are still figuring themselves out, and how HR leaders can coach founders into the practice.

Proactive leadership is the discipline of making decisions before they make themselves. Reactive leadership is the default in early stage companies because the next problem is always urgent. The shift from reactive to proactive is one of the most consequential leadership transitions a founder makes, and HR leaders are often the people who help them make it.

HR leaders should think about leadership coaching as part of the operating system of a young company rather than as a benefit. The companies that bake coaching into how leaders develop produce stronger executives, lower attrition, and better outcomes for the workforce as a whole.

Why proactive leadership matters most when companies grow

The behaviors that work at twenty employees do not scale to two hundred. Founders who personally know every employee, make every key decision, and respond to every issue cannot do that at scale. Without a deliberate transition, the company hits a ceiling that is structurally about leadership rather than market.

According to McKinsey research on the great attraction, leadership effectiveness is one of the strongest predictors of whether employees stay through a growth phase. Proactive leaders create the clarity that scaling teams need.

The HR job is to recognize the transition and coach through it. AllVoices supports the listening half through an engagement solution and a pulse survey product that gives founders a fast read on how the team is experiencing their leadership. Transformational leadership is built one feedback loop at a time.

Coaching founders through the transition

What does proactive leadership actually require?

It requires the leader to spend less time fighting fires and more time designing the systems that prevent them. Time on hiring, time on manager development, time on cultural reinforcement, and time on strategic clarity are the highest use uses of an executive's calendar.

The discipline is to protect that time when the urgent feels overwhelming. Founders who delegate fire fighting to capable managers free themselves for the work only they can do. The transition is uncomfortable. It is also necessary.

How do you coach a founder who resists?

Most founder resistance is not stubbornness. It is fear of losing the qualities that made the company work in the first place. Coaching that names the fear and offers a path that preserves what matters tends to land. Coaching works best when it is honest and concrete.

The peer evidence helps. Founders are often more persuaded by what comparable founders did than by what advisors recommend. A coach who can offer specific examples of similar transitions, with the trade offs visible, accelerates the work.

What actually works

Build the executive feedback loop

Founders rarely get honest feedback once the company crosses fifty employees. Direct reports defer. Investors give strategic input but not behavioral input. The feedback loop has to be built deliberately. 360 surveys for the executive team, run by an outside party, produce input that internal channels suppress.

The feedback only matters if the founder acts on it. Coaching that pairs the input with concrete behavior changes, reviewed quarterly, turns the loop into development. According to HBR research on turning feedback into action, the pattern of follow through is what makes feedback systems credible.

Train the manager layer in parallel

Proactive founders are bottlenecked by reactive managers. The leadership transition is incomplete until the manager layer can run their teams without escalating routine issues. Manager training that focuses on coaching, feedback, and decision making produces the layer the founder needs.

The investment is significant. The return is larger. A trained manager layer multiplies the founder's effectiveness rather than draining it. Management styles across the team should be coherent enough that employees experience consistent management even as they move between teams.

Communicate the operating model out loud

Most early stage companies operate on tacit assumptions that the founders share but employees do not see. Writing down how decisions get made, how feedback flows, and how performance is judged surfaces those assumptions and lets the company audit them. SHRM guidance on values based leadership reinforces that visible operating norms outperform implicit ones.

The operating model document is not a constitution. It is a working draft updated as the company learns. The discipline is keeping it current rather than writing it once.

Where Employee Relations Fits

Early stage companies often under invest in ER until the first incident reminds them why it matters. AllVoices supports the build through an employee relations function that scales with headcount and an HR case management product that gives HR a structured workspace from day one.

Why early ER investment pays back

The first significant ER case is also the first test of the company's process. Companies that have invested early handle it well. Companies that have not learn the cost of not investing. The blog on workplace misconduct covers what early investment looks like in practice.

Frequently Asked Questions About Proactive Leadership

When should a founder start working with a coach?

Earlier than most founders think. The transition gets harder, not easier, the longer the company runs without proactive practice. By the time the founder feels they need a coach, the team has often been waiting for one.

What if the founder will not invest in their own development?

The HR leader has limited ability to force it but significant ability to make the gap visible through structured feedback. Sometimes the data does the work the conversation cannot.

How does this work with co-founder dynamics?

Co-founder coaching often matters more than individual coaching. The relationship between founders sets the cultural ceiling. Working on it explicitly is one of the highest use moves available.

What is the right cadence for executive feedback?

Quarterly 360 surveys for the executive team, plus a monthly check-in with each leader's coach. The cadence keeps development continuous rather than episodic.

What is the biggest mistake?

Treating leadership development as something that happens after the company stabilizes. By then, the patterns are entrenched. The investment has to start earlier.

What's the first step for HR leaders who want to put this into practice?

Start with one team and one measurable outcome. Pick a function where the issue shows up sharply and a leader who is willing to model the new practice. Map the current state honestly: what is happening, who feels it, and what would good look like in ninety days. Share that picture with the team, ask them what is missing from your read, and adjust before launching anything formal. The goal of step one is alignment, not activity.

Once the picture is shared, pick two or three changes you can make inside one quarter. Resist the urge to launch a full program. Run the changes, measure the response with simple pulse questions, and report back. The combination of a focused team, a clear measure, and a public commitment to learn is what turns a good idea into a practice that spreads. HR leaders who try to launch everywhere at once usually end up launching nowhere.

Iterate from there. The teams that succeed treat the first cycle as a prototype, not a rollout. They keep what worked, drop what did not, and write down what they learned. By the time the practice expands to the next group, it has been pressure-tested by people who have a stake in seeing it work. That is the unglamorous work of putting any people-strategy idea into practice, and it is also the work that compounds.

The Bottom Line for HR Leaders

Jonathan Basker makes a useful argument that proactive leadership is the structural open up for scaling companies. Reactive founders create reactive teams. Proactive founders create the conditions for proactive teams.

The mandate for HR leaders is to recognize the transition early, build the feedback loops that make it visible, and partner with founders on the practice that makes it sustainable. Done consistently, the company graduates from heroic effort to systemic excellence.

See how AllVoices helps HR leaders build the listening systems that proactive leadership requires.