From Accidental to All-In: 6 Leadership Lessons from Ali Merchant

This post is from a conversation I had with Ali Merchant on episode #20 of The Learning to Lead Show.

Were you ever actually trained to be a leader, or did someone just hand you a team and wish you luck?

Sit with that for a second. Two out of three managers have never been trained to lead. If you put three managers in a room, statistically two of them are winging it, navigating their role through a combination of intuition, imitation, and hope. Not because they don’t care. Not because they lack ambition. But because no one ever taught them how.

Here’s what I’ve learned: the leaders who become exceptional almost never start that way. They start exactly where you started, in a role they weren’t fully prepared for. The difference isn’t talent. It’s intention.

That’s why I wanted to share what I learned from my conversation with Ali Merchant, author of The All-In Manager, leadership trainer, and executive coach. Ali has spent nearly two decades teaching more than fifteen hundred leaders worldwide how to move from accidental to all-in, and his framework is one of the most practical and human-centered I’ve encountered. Here are six of his most powerful lessons.

This article is from a conversation I had with Ali Merchant on episode #20 of The Learning to Lead Show. Ali is the author of The All-In Manager — a book born not from theory, but from lived experience.

He knows what it feels like to be handed a team with no warning and no training, and he turned that experience into a practical leadership framework that any manager can apply.

What struck me most about our conversation was how grounded and honest Ali was, no fluff, no corporate speak, just real talk about what it actually takes to build trust, create safety, and lead people well. If you're a leader who wants to stop flying blind and start leading with intention, you're going to get a lot out of this one.

The term “accidental manager” isn’t an insult. It’s a description of how most leaders actually arrive at leadership. You were good at your job. Someone noticed. They gave you people to lead. And suddenly you’re responsible for performance reviews, difficult conversations, team culture, and developing people, none of which your previous job prepared you for.

“Two out of three managers are accidental, meaning they’ve had no training, no coaching, no mentoring. They were just told: you gotta go do this thing.”

Being an accidental manager isn’t the problem, Ali says. Staying one is. Too many leaders simply wing it indefinitely — managing by instinct, defaulting to how they were managed, never closing the gap between where they are and where they need to be.

Ali’s answer is the All-In Manager framework: three non-negotiable commitments. All-in managers are insatiable learners, not just about industry trends, but about themselves. They deliver meaningful results, not just activity, but outcomes that move the needle. And they personally care for the success of their people, genuinely, not performatively. You need all three. One or two won’t do it.

Reflect: Honestly assess yourself against the three All-In commitments.

Where are you strongest — as a learner, a results-driver, or a people-developer? Where is your weakest link?

The gap between accidental and all-in isn’t talent. It’s intention.

What would it look like this week to be intentional in your weakest area?

Trust usually doesn’t collapse in one dramatic moment. It erodes through small withdrawals: inconsistency, broken promises, careless words, unmanaged emotions, and silence when people needed clarity.

Ali uses a picture every leader should keep in mind:

“Trust is like a bank account. You gotta keep adding those deposits.”

That framing is so useful because it tells you what to do next. Deposits are behaviors. Withdrawals are behaviors. It’s measurable.

And it takes pressure off perfection.

Ali made this point in a way leaders need to hear.

“If you become someone who is worthy of trust… even if you drop the ball and even if you make a mistake, your people will forgive you.”

The goal isn’t to never mess up. The goal is to build enough trust that when you do miss, your team doesn’t assume the worst.

Most leaders think of trust as a single thing. Keep your word. Show up when you commit. That matters, but Ali is clear: it’s only one leg of a three-legged stool.

1. Reliability.

• Will you do what you said you’d do?

2. Competence: because if you keep producing mediocre results, your team eventually stops trusting your judgment, even if they trust your intentions.

• Can I trust your judgment and execution?

3. Care: And this is where many highly capable leaders fall short.

• Are you for me… or are you using me?

“We know a lot of leaders who are very competent, really brilliant leaders. But they don’t care about their direct reports. It’s only about them, only about their goals, only about their agenda. These are brilliant people, but no one wants to be around them.”

Miss any one of these and trust gets shaky.

Ali gave a perfect example that exposes a blind spot:

“Imagine you are a very reliable person… But whenever you do it, you make a whole lot of mistakes… Do I trust you? That erodes the trust.”

Reliability without competence becomes frustration. Competence without care becomes cold. Care without reliability becomes chaos. Trust requires all three.

What makes this bank account metaphor so powerful is that the deposits aren't random acts of niceness; they're intentional, specific behaviors.

Dr. Henry Cloud, in his book Integrity, breaks trust down into three distinct building blocks: connection (people need to feel genuinely understood, not just managed), extending favor (showing up for people even on their worst days, not just when they've earned it), and vulnerability (sharing honestly about your own struggles so your team sees that hard seasons are survivable).

Cloud reminds us that the word "encourage" literally means to put courage into someone, and leaders who practice these three deposits consistently build the kind of relational reserve that weathers mistakes, misses, and hard seasons without the whole account going to zero.

Think about the leaders who have made the deepest impact on you. Chances are they weren’t just competent or dependable. They made you feel like your success mattered to them personally. That’s the third leg. Without it, the stool tips.

Here’s what struck me: your direct reports are sizing you up constantly. They’re asking three quiet questions.

• Can she actually do this job?

• Will he do what he says?

• Does she genuinely care about me?

If the answer to any one is no, everything built on top of trust suffers with it.

Reflect: Which leg is your strongest right now, reliability, competence, or care?

Which is wobbliest? Ask someone who reports to you to rate you honestly on all three.

What you learn might be uncomfortable. It will also be the most useful leadership data you receive this year.

Here’s a question worth reflecting on:

What are your best people not telling you?

Not because they don’t know. Not because they don’t care. But because they’ve calculated, correctly or not, that the risk of speaking up outweighs the benefit. So they stay quiet. And their best thinking stays locked inside them.

Ali calls this psychological safety: a climate where people feel safe enough to take interpersonal risks. To disagree. To say “I don’t understand.” To challenge an idea, even the boss’s idea. He points to Netflix’s 2011 Qwikster decision, the company split, the prices raised, the stock that collapsed, and the millions of subscribers who fled. The part most people don’t know: employees had serious concerns before launch. And they said nothing.

“What if my idea is stupid? What if Reed Hastings thinks that’s not a great idea and shoots it down? So they stayed quiet … even in a great company like Netflix.”

That’s what a psychologically unsafe environment costs you. Not just morale. Real money. Real decisions made with incomplete information. Real innovations that never see the light of day. The research is consistent: teams with high psychological safety don’t just report higher satisfaction; they produce measurably better results. Safety isn’t the opposite of performance. Safety is what makes sustained performance possible.

Reflect: Do people on your team regularly challenge your ideas, admit mistakes, or ask questions when they’re confused, or do they mostly agree with you and stay quiet?

If you’re not sure, that uncertainty itself is worth paying attention to. What’s one thing you could do this week to actively signal that honest input is genuinely welcome?

Candor is one of those leadership words that everyone agrees with in principle and struggles with in practice. Ali’s concern isn’t that leaders don’t value candor; it’s that the word has been hijacked. Some bosses believe that in the spirit of being candid, they can say anything. The result is a culture of brutal honesty that’s all brutal and not much honest, where directness becomes a permission slip for unkindness.

True candor, Ali insists, is clear, direct, and kind simultaneously. Those aren’t competing values. They’re all required. He makes it concrete with a story from his own career, passed over for promotion while his peers advanced. His boss called him in and said something Ali still carries with him:

“I have higher expectations from you, Ali. Right now you haven’t met those expectations, and that’s why we’re not promoting you. But I’m going to sit with you. We’re going to get you where you’re trying to go.”

It was hard to hear. It was also one of the most valuable things anyone had ever said to him, because it was honest, specific, kind, and forward-looking.

To build a candor culture, Ali recommends three moves.

1. Set the expectation explicitly, give your people permission to speak up and mean it.

2. Define the rules together, face-to-face, specific, timely. No passive-aggressive emails, no public humiliation.

3. Reward it. When someone shares a difficult truth, your response in that moment either builds the culture or breaks it. “Tell me more” builds it. “You’re wrong” breaks it.

Reflect: Has your team defined what acceptable candor looks like, specifically, behaviorally, by mutual agreement?

Or are you operating on an implicit standard that nobody has ever made explicit?

What would it look like to have that conversation with your team this month?

Ali names difficult conversations as the number-one struggle he hears from leaders across the globe. Senior leaders. New managers. CEOs. It doesn’t matter the level. Almost everyone finds them hard. And almost everyone avoids them far longer than they should.

He describes two failure modes.

1. The avoider does everything but talk to the person, tells their spouse, calls their best friend, maybe brings it to a coach, but never talks to the one person with the power to change anything.

2. The impulsive goes the other direction, shooting from the hip, delivering judgment without specifics, making the conversation about character rather than behavior.

3. The responder is in the middle: specific, behavioral, timely, and kind. Not easy. But learnable.

“Difficult conversations don’t ruin relationships. Avoiding difficult conversations typically tends to ruin relationships.”

And there’s a collateral problem most avoiders don’t see. Your top performers are watching. They see the leader avoid accountability. They see the low performer get away with it. And over time, their respect erodes, until the day your best person walks into your office and tells you they’ve found something else. Not because of the problem coworker. Because of the leader who wouldn’t address it.

The antidote is straightforward, if not easy: be tough on the problem, tender on the person. Address behavior, not character. Be specific. Be timely. Be kind. And have the conversation you’ve been avoiding.

Reflect: Is there a conversation you’ve been avoiding right now? Be honest. Who on your team needs honest, direct, kind feedback that you haven’t given them yet?

What has the cost of that avoidance been, to them, to the team, and to you?

What would it take to have that conversation this week?

Stay with me here, because this is the principle that quietly threads through everything else in Ali’s framework.

Leaders who are great at their jobs are often great because they’re great problem-solvers. They see an issue, and they solve it, fast, effectively, satisfyingly. And that’s exactly what makes them dangerous as leaders. The more they solve, the more their team learns to bring problems to them rather than develop the capacity to solve problems themselves.

Ali’s advice is counterintuitive: become lazy. Not disengaged, strategically lazy. Resist the urge to be the fixer. Ask a question instead.

“Learn to listen. Learn to ask a great question and learn to shut up and listen to the answer. That will serve you for the rest of your life. I will bet any amount of money on that.”

This is the unifying thread beneath every other lesson. Psychological safety is signaled most clearly when a leader responds to a challenge with “Tell me more.” Debate-making, Ali’s practice of inviting your team to poke holes in your biggest ideas- is built on six words:

Can anyone poke holes in this?

Feedback conversations are built on, “What is one thing I can start doing differently?”

A well-crafted question does something an answer can’t: it develops the thinking of the person you’re asking. It builds their capacity. And over time, it produces a team that can function without needing the leader to solve everything. That’s not laziness. That’s multiplication.

Reflect: What is one question you could ask someone on your team today that you’ve never asked them before, a question that might genuinely surprise them and open a new conversation?

Write it down before you close this article. Then ask it. The answer might be the most valuable thing you learn this week.

Ali started reading a Tony Robbins book in a dorm room at Arizona State, trying to make sense of a new country and a new life. He became a manager overnight, with no preparation and no roadmap. And he chose, in that moment, to figure it out. That choice, to go all in rather than stay accidental, has defined everything since.

The principles here aren’t abstract ideals. They’re practices, things you can do today, this week, in your next conversation. Build trust on all three legs. Create a climate where people feel safe to be honest. Have the conversation you’ve been avoiding. Ask great questions and sit with the answers.

It’s simple. It’s common sense. And as Ali says, it’s not common practice. That gap is the opportunity. And it’s available to every leader willing to go all in.

Pick one principle from this list, just one, and put it into practice this week. Not all six. Just the one your gut already knew you needed when you read it.

• Ask a direct report which leg of trust you most need to strengthen.

• Invite your team to poke holes in a plan you’ve already half-decided on.

• Ask one vulnerable feedback question, and just listen.

• Schedule the difficult conversation you’ve been postponing.

Whatever it is, take the step. That’s how all-in leaders are built. One intentional decision at a time.

Go out this week with a humble curiosity to learn, grow, and lead, taking your team to the next level.

• "From Accidental Leader to All-In Manager," Ali Merchant's Leadership Journey

• Multipliers — Liz Wiseman

• No Rules Rules: Netflix and the Culture of Reinvention — Reed Hastings & Erin Meyer

• Zen and the Art of Firefighting — on leading under pressure

• Giant Steps — Tony Robbins (the book that started it all)