If you're building a company, knowing your role isn't optional. The visionary needs someone who will build what they see without getting in the way of the seeing. The integrator needs someone who will point at the moon and mean it and keep pointing at the same moon long enough for the bridge to get built. The mistake I see most often: trying to be both or hiring someone who mirrors you when you need someone who complements you.
Read MoreThe fear of success doesn't usually announce itself as fear. It sounds like planning. It sounds like due diligence. It sounds like being responsible.
What it actually is: A limiting belief. It’s spending today's energy on problems you'll only face if you win
Read MoreDon't prevent scraped knees; prevent bus crashes. A scraped knee hurts. You might carry the scar for years. That's the point. The pain is proportional to the lesson. A bus crash can lead to catastrophic loss. The project. The company. The relationship. Something that can't be recovered. The leader's job isn't to eliminate mistakes. It's to know the difference between those two things.
Read MoreThe leader's job isn't to have the answer. It's to create conditions where the best answer can emerge. That means encouraging disagreement without punishment. Creating opportunities for information to move across functions. Making it safe for people to challenge assumptions, including your own. The highest-performing teams in these simulations don't succeed because they have the smartest leader. They succeed because nobody in the room is waiting for one person to have all the answers.
Read MoreThe leaders who are consistently good at managing up and across understand something most people miss: influence gets built long before it’s needed. Not through charisma. Not through politics. Through small, deliberate actions repeated consistently over time. Investments. Relationships are like a bank account. You have to make deposits before you can make withdrawals. Most people get this backwards.
Read MoreThe leaders who build something lasting lead differently. They retain great people, create cultures that outlast them, and build organizations that can function without them. They share power. They create it in others. When a team operates out of fear of authority, they do the minimum required to avoid consequences.
Read MoreWhen a leader tells me their team has an accountability problem, I don’t start with the team. I start with asking the leader questions. In fifteen years of coaching founders and executives, I’ve found that accountability is almost never the root problem. It’s a symptom. And until you find what’s underneath it, you can replace people, run workshops, post core values on the wall, and the same problem will keep showing up with different faces.
Read MoreMost founders hit one of two walls. The first is scale. The second wall is the opportunity to exit. Stuck means you can’t grow. And you can’t leave. There are a few ways through. The first is triage. The second is investment. The third is time.
Read MoreMost founders built their business from nothing. They were the product, the salesperson, the decision-maker, the culture. The company exists because they willed it into being. Somewhere along the way, being needed became part of who they are. That's not ego in the pejorative sense. It's human. We find meaning in being useful, in being the person others turn to.
Read MoreHere’s what I’ve noticed about the leaders who wait. They’re not unaware. They’re not ignoring obvious problems. They see them. They just learn to live with them. Margins tightening a little each quarter. A team dynamic that feels slightly off. A process that’s inefficient, but still works. None of it is broken enough to force action. So it waits. And while it waits, it becomes the new normal.
Read MoreYou can pull data instantly, generate a strategy in seconds, and pressure-test your thinking with something that sounds confident and coherent. And still walk away with the exact conclusion you started with. Not because the tools are broken. Because they're flexible. Give ten leaders the same data and they'll reach ten different conclusions. Give them AI, and each one can explain why they're right.
Read MoreAnxiety isn't new. The volume is. More inputs. More uncertainty. More decisions. Less time between them.
You can't eliminate that. You can manage how you respond to it. Recognize something most leaders don't say out loud: If this feels harder than it used to, it probably is.
The goal isn't to remove the pressure. It's to make sure it doesn't start making decisions for you.
Read MoreFor years, leadership advice was straightforward. Set the vision. Pick a point on the horizon. Steer toward it. Adjust for obstacles, but do not lose sight of where you are going. That advice assumes you can see the horizon. Right now, many leaders cannot.
The long term did not disappear. It accelerated.
Read MorePositivity becomes toxic when it feels forced. When it ignores obvious problems. When it discounts what people are feeling or seeing. Most of the time it is not about morale. It is about discomfort. Leaders reach for positivity when they don't want to sit in the tension of a hard situation. If everything sounds upbeat, maybe the problem feels smaller. It doesn't.
Read MoreEmotionally, walking away from a past loss feels worse than risking a future one. Psychologists call this loss aversion. People feel losses more intensely than equivalent gains. A million-dollar loss feels catastrophic in a way a potential million-dollar gain never will. That is why leaders keep pouring resources into failing projects.
Read MoreWhen someone says or does something that bothers you, there's a fork in the road. One path is judgment. The other is curiosity. Judgment is faster. It feels decisive. Especially under pressure. Curiosity takes more time. It requires vulnerability. It risks hearing something you don't like. So most leaders default to judgment.
Read MoreFounder mode is neither good nor bad. Hustle is neither noble nor toxic. The real question is simpler and harder. Is the urgency coming from the needs of the business, or from the wiring of the founder? I see this constantly. Founders who built successful companies and cannot break through the next level of growth. Not because they stopped working hard, but because they never stopped working the same way.
Read MoreEntrepreneurs who build traction almost always skew urgent. That urgency is often what gets the company off the ground in the first place. At scale, that same instinct becomes disruptive. People struggle to understand priorities. Context switches constantly. Everything sounds like a crisis. Leaders start mistaking urgency for accountability and patience for disengagement. So founders hire someone to "balance" them. Often a COO, Chief of Staff, or operations leader who skews more patient. In theory, it's a purposeful pairing. In practice, it creates conflict.
Read MoreStrong cultures don't eliminate toxicity entirely. They detect it early and contain it fast. They have antibodies: clear values, frequent feedback, leaders who stay engaged even under pressure. The goal isn't perfection. It's resilience. Whether a single bad apple spoils the barrel is one of the clearest indicators of leadership quality
Read MoreMany leaders do the same thing with every hard decision. If you’re waiting for the right time, you’ll never act. There is no perfect information. There is no risk-free moment. There is no version of this that doesn’t require courage. Make the decision. Or don’t. But stop pretending indecision is neutral.
Read MoreStartups and Small Businesses sometimes find themselves at the edge of a chasm. With success in developing and growing their business, a stage is reached where they find that the "next step" is a big one! Trajectify partners with the entrepreneur to build momentum and trajectory to be able to cross the chasm.
We offer private and group (Mastermind) coaching and hold frequent events and seminars.
Trajectify is founded my Mike Krupit, veteran of eight startups. Mike has helped dozens of companies grow and mentored and advised hundreds more.
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