The Leadership Style That Gets You Here Won't Get You There

IN the early stage of an enterprise software startup, the founder is often the best - and main - salesperson. And that makes sense – founders have the deep product knowledge, intuitive understanding of the market, and heartfelt enthusiasm to win over customers, even when they thought ‘sales’ wasn’t really their thing. But if you want to scale up, at some point founder-led sales are going to hit a ceiling, and founders have to work out how to transition to a different model.

This can be difficult: Intuition, improvisation, and sheer force of character often work to get deals over the line when a founder is the one working with the customer, but it is very hard to recreate once they pass the torch.

The foundational principle of my go-to-market framework – which I detail in my new book, Built to Grow: A Handbook for High-Performance Sales Teams – is that every startup passes through three distinct phases on the road to success.

First, you experiment with the tactics that will form the bedrock of your business. Second, you build systems and processes that create a repeatable and sustainable business. And then you scale everything: you hit the gas pedal and accelerate, investing heavily to drive growth.

When it comes to sales, founders and CEOs play a different role and must have different priorities in each of these phases. The approach that gets a business going isn't the same one that will get it to $100m in sales. Here's the roadmap founders need to follow.

Experiment

At this stage, no one knows better than the founder how to sell the product. The imperative during the early stages of building a go-to-market strategy is for founders to think very hard about how they can replicate themselves. The best way to do this has two components:

First, founders should experiment with, identify, and document their ‘repeatable sales motion’: the winning strategies and tactics that have enabled them to successfully sell in the early days.

In parallel, they should bring their first two or three ‘trailblazer’ sales hires on board who can experiment with them, and work out how to evolve their more improvised sales approach into this repeatable sales motion. Some of the important questions to ask here are: “Who is my ideal customer and where do I find them? What are their pain points and how do I communicate with them? And how do I best support their buyer’s journey, step-by-step, and close a sale with them? Writing all this down will create the company’s first brief sales playbook–a cornerstone of a startups GTM strategy.

During this early, experimental phase, founders are going to stay very involved with sales, alongside those key trailblazer hires. Once they have all this formally documented in their first, albeit brief, sales playbook, and 2 or 3 non-founder salespeople hitting quota, they graduate from ‘Experiment’ to ‘Build.’

Build

During the build phase - going from 3 to 8 or 9 salespeople - the founder or CEO’s goal is to pressure-test their repeatable sales motion and to prove that non-trailblazer salespeople can use the newly written playbook to successfully sell the product. They also lay the foundation for sustainable growth and operational excellence. This means establishing best practices for revenue management – which comprises opportunity management, pipeline management, and forecasting.

At the same time, you keep expanding the sales playbook - and if the newly hired salespeople are struggling to hit quota, you need to debug your approach. Are you not targeting the right type of customer? Is your messaging, pricing, or packaging wrong? Or maybe you haven’t hired the right profile of salespeople, or not trained them well enough?

The only way to grow sustainably is to keep refining the playbook until you prove that all non-trailblazer salespeople can use it to successfully sell and hit quota. This will allow you to transform sales into a disciplined function rather than an improvised and inconsistent art form. What you want to avoid at all costs is one day in the future having 30 salespeople who are each experimenting in their own way, doing their own thing, and thus making quarterly sales targets a gamble.

Founders are still pretty involved at this stage, but a big part of the build phase is preparing to be more hands-off later – establishing a dedicated head of sales and a fairly senior sales operations leader. Both of them will also continue to help select and integrate the right AI-supported sales tools for the growing sales team.

There's a balancing act here: founders want to hand over day-to-day management of the sales function, but remain close to their customer and their newly hired sales leader to understand if they have hired the right person for the job.

When the company has seven or eight dedicated salespeople that are able to use the sales playbook to reliably hit quota, it is ready for the next step.

Scale

This is the big one. If you have 7 or 8 salespeople reliably hitting quota, you are likely on to something, and it’s time to invest and take the market. In Scale, you're building from eight to 100 or more salespeople, and an $80m or $120m company has to be run differently from a $20m one. Everything changes in this phase, and sales productivity and efficiency become the name of the game. Think about it: If you have 80 salespeople, it makes a huge difference if each salesperson has 3 customer meetings per day versus 6 customer meetings per day.

The founder or CEO really can't be involved in the day-to-day management of the sales team at this stage. Now, they must rely on their sales leadership, specialized sales teams, and distinct customer success, sales enablement, and operations functions. That said, the founder still needs to understand enough about how a well-run revenue organization should function. As a founder or CEO you don’t want to be left surprised when your sales leader isn’t hitting their revenue targets until the end of the quarter, when it’s too late to take action.

A big failure mode for startups is being too slow to mature their management style and capacity at this stage, so founders need to be very clear-eyed about their management team. As they scale, they need to make sure they have enough executive horsepower in each of their functions and hire accordingly. Founders need to be intentional about building the right management team to have by their side for the crucial and intense years to come. For many, this is the time when founders have no choice but to significantly upgrade their go-to-market leadership. In parallel, founders should place extra focus on protecting the customer experience, which is one of the first things lost when a company suddenly starts to grow very quickly.

Getting a startup on track for a successful IPO or acquisition–or to become a large, independent private company–can be a long and difficult journey. But with the right go-to-market strategy, a successful pivot from founder-led sales to a repeatable, playbook-based sales motion, and a conscious focus on revenue fundamentals, startups can give themselves the best possible chance of reaching take-off velocity.

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Stephanie Friedman is an angel investor and adviser to startup founders. Built to Grow: A Handbook for High-Performance Sales Teams will be published by Stripe Press on October 13.

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Posted by Michael McKinney at 12:27 PM
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Leading Thoughts for October 08, 2026

IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with:

I.

Ryushun Kusanagi on living in the now:

"Clinging to the past and using it as a reason to negate the present is a mental trap-a distraction from what truly matters, and a source of inner turmoil. Life is full of missteps and failures. What matters is how you respond to them. Don’t dwell on your mistakes. Don’t beat yourself up. Don’t look back in regret. Don’t give in to pessimism. Instead, focus on the present, understand it correctly, and dedicate yourself to what you can do right now. Of course, if you’ve hurt someone, it’s important to acknowledge it and sincerely apologize. Doing this is part of taking responsibility. Embrace that moment and take the opportunity to start afresh."

Source: The Practice of Not Reacting

II.

John Maxwell on not taking sides:

"If you’re a leader and you allow yourself to get drawn into taking sides and working against other groups of people, you’re limiting your leadership. As leaders, we all need the people on the other side. Our side doesn’t have all the answers. Believing we do is arrogant. I’m not always right, and neither are you. And those on the “other side” are not always wrong. If you don’t listen to them, you’re shrinking your influence and limiting your impact. If you can’t work with people who disagree with you, you will never become the leader you could be. No one will ever convince me that you can choose only half of the people and get as much done as if you work to lead all the people."

Source: High Road Leadership: Bringing People Together in a World That Divides

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Posted by Michael McKinney at 11:02 AM
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How to Respond When People Throw Wrenches During Change

CHANGE initiatives rarely fail because of flawed strategies or poor execution. They fail because of human behavior: what people do when they feel threatened or at risk of losing status, control, or relevance. A senior leader withholds resources from another team. A project team member hoards information about transition status. Each move undermines the initiative's success. When combined with others, they can derail it.

These are the wrenches people throw during high-stakes change. They can be hard to spot and address because they are often covert, uncoordinated, and unpredictable. Without quick and effective responses, dysfunction grows and plans unravel. Left unchecked, the self-interested behaviors become cultural norms, and the downward spiral to failure accelerates.

Why People Throw Wrenches During Change

Change initiatives typically start well. The leader’s vision of a better future is clear and widely supported. The kick-off builds momentum, and work begins. Before long, people piece together their relative position in the post-change organization.

Employees view disruptions through the lens of personal gain or loss. What will this mean for my role, status, influence, or security? As the answers become clearer, emotions flare, which drives actions intended to improve their position.

Four forces explain self-interested behavior:

• Self-preservation: People try to protect the status, certainty, freedom, camaraderie, and confidence they have.
• Power: People seek the capacity to influence outcomes. They do so through formal authority or personal influence. Change can threaten existing power sources or create opportunities for new ones.
• Politics: People maneuver to influence those who define the future ways of working. Alliances, favor trading, and even rumors can modify outcomes.
• Emotions: Anxiety, fear, frustration, anger, and contempt can harm colleagues and jeopardize the initiative. When emotions surface, self-protection outweighs concerns for others and their organization.

All four forces can be in play at any point in an initiative, so leaders need to anticipate them. Understanding what people perceive they will lose helps you predict likely self-interested behaviors and decide how to best address them.

The Wrenches We Throw

The most common self-interested behaviors vary in their intensity and the risk they pose to an organization. They fall into four categories, based on strategic intent and level of disruption: Influencing, Conspiring, Bullying, and Sabotaging.

The tactics are more extreme as you move to the right of the continuum. Influencing and conspiring are about angling for position, whereas bullying and sabotaging behaviors are about aggression to seize control.

These behaviors also evolve as the initiative progresses, because each phase of change reveals more about what people stand to gain or lose. During the planning phase, there are few details to analyze. Preparation activities such as testing, training, and day-in-the-life exercises begin to clarify future conditions. The full picture emerges after the launch when people live and feel their new roles. The clearer the personal consequences become, the stronger the emotional response, and the greater the likelihood of more aggressive behavior.

Responding When Wrenches Appear

When a political maneuver or power play catches us off guard, we often become spectators instead of responders. Silence, or a defensive reaction, can strengthen the behavior and increase its damage.

A consistent, stepped process, designed to interpret people’s behavior, helps you neutralize self-interested tactics. The Four-Step Response offers a simple approach to recognizing and responding to political maneuvers and power plays: Observe, Assess, Select, and Deliver.

1. Observe: Notice what the person says and does. If someone says, “I’ll support your region if you support mine when resources are allocated,” they are favor trading.
2. Assess: Identify the emotion that may be driving the behavior. Anxiety and anger call for different responses. Anxiety signals worry about uncertainty, whereas anger signals hostility over a perceived injustice or error.
3. Select: Choose the response best suited to the behavior and the circumstances around it. Consider the person’s role, the emotion they are feeling, and where the behavior surfaced.
4. Deliver: Give your response, then pause for a reaction. The behavior may stop. If not, their response will indicate your next move, whether to hold, engage or escalate.

If, for example, a team member repeatedly withholds information, an effective response might be to name the behavior directly: “The testing team needs the data we agreed to share. Without it, testing will be delayed. What is preventing you from providing it?” Their response may reveal a technical obstacle or a fear about losing control. Both guide how to proceed.

Following these steps helps you spot self-interested behavior early, identify the emotion behind it, and respond in ways that protect your credibility, relationships, and results.

We All Throw Wrenches

It’s easy to view people who withhold information, spread rumours, or blame and attack as villains. The reality is that we all throw wrenches when change threatens us. It's normal, and it’s human. Knowing what you personally stand to gain and lose can help you manage your behavior and respond better to others' actions.

You can’t control the wrenches thrown or the people who throw them. You can control how you respond. Observe the behavior, assess the emotion driving it, select the best option, and deliver it with purpose to protect the initiative’s progress and results.

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Phil Buckley is a change strategist and leadership advisor with 35 years of experience across 32 large-scale change initiatives in the United States, Canada, and the United Kingdom. He is the founder of Change with Confidence and author of Change on the Run, Change with Confidence, and his latest book, When People Throw Wrenches: Navigating the Emotions, Politics, and Power Plays of High-Stakes Change. Learn more at www.changewithconfidence.com.

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Posted by Michael McKinney at 06:11 PM
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Leading Thoughts for October 1, 2026

IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with:

I.

Brady, Kliman, and Smith on seeing the full story:

"We feel strongly that empathy and humility aren’t distractions from value creation; they’re the drivers of value creation. In fact, they’re essential if we want to lead difference-filled teams that solve problems creatively, build trust across difference, and adapt in real time to new challenges. These aren’t soft skills. They are strategic capabilities for a complex world. Empathy, the emotional engine behind perspective-taking, is where real understanding begins. Without empathy, it’s impossible to truly see another person’s point of view, because you wouldn’t care enough to try. Empathy and humility ground us in the understanding that we don’t possess all the answers and that other people’s experiences matter just as much as our own in terms of making sense of any situation."

Source: All the Difference. Six Leadership Actions to Bridge Perspectives, Strengthen Teams, and Create Value

II.

Jim Schleckser on peanut buttering:

"A lot of the mediocre and hardworking CEOs we have run into over the years are exceptionally good at what we call ‘peanut buttering.’ When it comes to allocating their time to the various tasks and stakeholders in their businesses—their boards, their supply chains, their investors, their communities, etc.—these CEOs do their best to spread their time as evenly as possible across all of them. The concern, of course, is to make sure everyone feels like they’re getting the CEO’s attention. In this effort, the CEO will work very hard, sometimes as much as eighty or more hours a week. The bad news is that this is the surest way possible to dilute the CEO’s impact on any one issue. Unfortunately, this concept of tending to every stakeholder is taught at many major business schools, which only perpetuates the error. This is done, in part, because CEOs aren’t certain what actions will drive the business forward; consequently, they work on all fronts, hoping one will yield results."

Source: Great CEOs Are Lazy

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Posted by Michael McKinney at 04:48 PM
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First Look: Leadership Books for October 2026

HERE'S A LOOK at some of the best leadership books to be released in October 2026 curated just for you. Be sure to check out the other great titles being offered this month.

The Mattering Effect: Creating a Life of Meaning and Worth by John R. Miles

If you’ve ever wondered, If I stopped performing, producing, fixing, achieving, proving, would I still matter? then this book is for you. As John R. Miles explores The Great Erasure happening in our lives―the sense of loneliness and disengagement despite outward success--he also provides a way for you to remember that you mattered before any professional or personal titles or achievements. Miles examines the cultural shift that has replaced human significance with human usefulness, resulting in exhaustion, self-erasure, and quiet despair. Where others have also diagnosed the symptoms, Miles identifies a deeper cause and offers a solution through M.A.T.T.E.R., a research-based framework grounded in six elements―meaning, autonomy, trust, time, energy, and reciprocity―that, when used together, can restore sustainable significance, dignity, and spiritual coherence.

Lead with Quiet Confidence: A Practical Guide to Success for Introverts by Jennifer Marcou

As an introvert, you can become an influential, confident, and authentic leader, without pretending to be extroverted, without performing, and without draining your energy. You don’t need to be the loudest voice in the room to be a powerful leader. Introverted professionals often bring deep thinking, strategic insight, and calm influence. Yet, our strengths can be overlooked in systems built around extroverted norms. Becoming a strong leader is not only about capability; it’s about how your capability is perceived. For introverts, this creates a unique challenge. We don’t lack for capability or value, but may feel insignificant because our significance is expressed in ways that often go unappreciated and underestimated in traditionally extroverted environments. In Lead with Quiet Confidence, you’ll discover research-aligned tools for introverted leadership, quiet influence, and authentic confidence-building:

In Person: How Working Together Fuels Creativity, Productivity, and Growth by Natalia Emanuel and Emma Harrington

For the first time in history, millions of workers can do their jobs from anywhere—and the result is the most contentious workplace debate in generations. Employees fight to protect their freedom. CEOs issue return-to-office mandates by gut instinct. Everyone argues, but no one has the data. Until now. Harvard-trained economists Natalia Emanuel and Emma Harrington are leading researchers on remote and in-person work. They've spent years tracking millions of work hours across industries, analyzing Fortune 500 firms, startups, tech companies, and call centers. Their findings? Remote work is good for crossing tasks off a to-do list, but can erode the quality of our work, stifle creativity, and hurt mental health. When we're together, our brain-to-brain synchrony increases 10x, accelerating creativity, mentorship, and innovation. That’s why Pixar animators, Nobel Prize winners, and Silicon Valley founders have come up with their best ideas face-to-face with one another.

Vibe: The Secrets of Strong Connections in a Lonely World by Adam Grant

When we vibe with other people, it fuels our happiness and success. Yet building meaningful ties is one of the most pressing problems of our time. As face-to-face interaction gives way to digital screens, communication gets outsourced to AI, and the world becomes more polarized, our loneliness crisis shows no signs of slowing. To reveal how we can forge faster, stronger, and longer bonds, Adam Grant offers groundbreaking studies, expert insights, and myth-busting stories. Filled with the eye-opening takeaways that have brought millions of readers to his books, Vibe teaches us that similarity is not necessary for solidarity, chemistry doesn’t always happen quickly, and closeness doesn’t always take time. Vibe will change how you interact with people. No matter how good you are at connecting, you can always get better—and help others get better too.

Reinvention at the Top: The Playbook for CEOs to Lead Under Pressure by Andrea Petrone

Most CEOs reach the top by mastering performance, yet few define who they are as leaders. In Reinvention at the Top, CEO Executive and Performance Coach Andrea Petrone addresses the silent identity gap that emerges at the highest levels―helping leaders stop performing the role and start leading as themselves. Andrea introduces the The Throughline Framework, a practical methodology for clarifying who you are, crafting a message that moves people, and leading with authentic presence. Drawing from over 20 years advising CEOs and Senior Leaders of Fortune 500s, mid-caps, and high-growth companies, this book provides actionable tools for navigating new roles, major transitions, and legacy-defining decisions with clarity and conviction.

Human Leadership: The Courage To Face Ourselves And Each Other by Kristen Hadeed

For more than a decade, Kristen Hadeed defined herself as a servant leader. As the founder and CEO of a company widely recognized for its compassionate culture, she made sure her people came first, always. But after years of pouring everything she had into her business and her leadership, Kristen came face-to-face with a hard truth: Behind closed doors, she felt trapped beneath the weight of carrying it all. She had built a career around putting others first and abandoned herself in the process. The work she once loved was now tangled up in a web of pressure and expectations. From the outside, she appeared to have it all together. But inside, she was falling apart. Human Leadership is Kristen’s raw, personal account of losing herself in service to others and the difficult work of finding her way back. It’s a story of burnout, ambition, resentment, grief, reinvention, profound self-examination, and the courage it takes to share what you discover with the people around you. By learning to face herself, tell the truth, and take ownership of her choices, Kristen became a more courageous, compassionate leader and built a life and business that would take care of her, too.

“Books are the quietest and most constant of friends; they are the most accessible and wisest of counselors, and the most patient of teachers.”

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Posted by Michael McKinney at 11:54 AM
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LeadershipNow 140: September 2026 Compilation

Here is a selection of Posts from September 2026 that you will want to check out:

• The Biscuit Story: A Lesson in Leadership From the Antarctic via @AdmiredLeaders
• Words That Change the World by @KevinPaulScott
• Leading with Inquiry (How to Have a Better Dialogue) by @EdBatista
• Slumps via @LeadershipMain
• When Every Choice Costs You Something by @PhilCooke
• Why Does Originality Feel So Rare in a World Full of Ideas? by @UX_Person Abigail Aghaibie The willingness to sit with a problem long enough for our own idea to emerge.
• 5 Ways The Greatest Leaders Reproduce Themselves by @BrianKDodd
• Why Speaking Up Doesn't Always Make You More Visible by @SusanMazza
• Be a Ford, Then a Sloan by @SahilBloom
• Authenticity Has a Moodboard Now by @shrutisitara We didn’t kill authenticity. We hired a creative director for it. Have we done this in leadership as well?
• Stuff happens. Where you look matters. How your Locus of Control affects your success. by @artpetty
• Why the Best Communicators Repeat Themselves by @PhilCooke
• What’s Happening to Wonder? by @Julie_WG AI can deliver answers in seconds, but what might we lose when we stop sitting with questions long enough to wonder?
• The Great Delayering Is Solving the Wrong Management Problem by @artpetty
• From Structure to Breakthrough: The 5-Step Leadership Chaos Formula by @BrianKDodd
• Always Encouraging, Never Discouraging by @jamesstrock

See more on Twitter.

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Posted by Michael McKinney at 07:59 AM
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Leading Thoughts for September 24, 2026

IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with:

I.

Richard Hagberg and Tien Tzuo on strategy:

"How do you know when your strategy is working? When your employees wake up in the morning knowing (a) why they are working for your company, (b) what the corporate strategy is, and (c) how they can contribute to that strategy by achieving specific goals and objectives. That’s the ideal green light situation."

Source: Founders, Keepers: Why Founders Are Built to Fail, and What it Takes to Succeed

II.

Geoff Tuff and Steven Goldbach on improving the process:

"The problem with best practices is that, by definition, if everyone around you follows the same best practices, they are no longer best. They are average. And what business leader wants to be average? The playbooks of business that have been crafted over decades yield an approach to management that is more concerned with risk mitigation than delighting customers and staying ahead of accelerating change. Many of these are so ingrained in business habits that there is no explanation for why we do things the way we do beyond ‘Well, that’s just how we do things around here.’"

Source: Hone: How Purposeful Leaders Defy Drift

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Posted by Michael McKinney at 07:28 AM
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Leading Thoughts for September 17, 2026

IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with:

I.

Marshall Goldsmith and Mark Reiter on inertia:

"Our default response in life is not to experience meaning or happiness. Our default response is to experience inertia. We think of inertia as the state of being inert or motionless—one of our purer displays of passivity and disengagement. It's not. Inertia is an active event in which we are persisting in the state we're already in rather than switching to something else."

Source: The Earned Life: Lose Regret, Choose Fulfillment

II.

Sebastian Wernicke on data objectivity:

"It's easy to understand why one would intuitively view data as a kind of 'objective truth.' After all, we assume that data originates from objective measurements, making the resulting numbers clear and unequivocal. However, capturing our reality in numbers is rarely straightforward. Defining precisely how we arrive at a number isn't mere nitpicking, as these choices can carry significant consequences when we use that number to make a decision. Fundamentally, there is no single 'right' method to translate reality into data. Usually many valid methods exist, but each will turn the facts into a different number. Data compresses a subjective view of the world. Those who look at data see not an objective truth but rather a specific (hopefully at least consistent and documented) interpretation of the world, expressed as numbers."

Source: Data Inspired: Building an Organizational Culture of Inquiry for Lasting Transformation

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Posted by Michael McKinney at 05:46 PM
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