How to Win Your First 100 Days as a Leader—With a Free Checklist to Guide You

Taking on a leadership role places enormous pressure to get things right from day one. Early decisions can rapidly build credibility or cause irreversible damage. 

To dig into how to navigate these crucial early days, we talked to Bill Canady, author of From Panic to Profit—who’s successfully steered billion-dollar organizations through turnarounds and explosive growth. 

Bill lays out exactly what separates effective leaders from those who falter: clear communication, bold decision-making, and relentless focus on execution.

He shares a checklist for leaders who want to dodge pitfalls and drive meaningful results right from day one. You can download the 'First 100-days Checklist' here.

1.“You emphasize the importance of having a clear, laser-focused mission. In your experience, how can leaders create and maintain a vision that resonates with their teams, especially during challenging times?”

Ensure that the mission aligns with the vision, and that both vision and mission drive everything the organization says and does, including its financial goals, strategic focus, internal and external messaging, brand, the structures that enable and focus the efforts of everyone, and the action plan in place. Staying aligned on strategy and being on pace with its execution unite the organization in its vision and mission.

2.“How do you ensure that all teams are fully aligned around a single strategy, and what common pitfalls should leaders avoid in this process? Can you share an example where your system helped you take action despite missing pieces of the puzzle?”

Not surprisingly, communication is key to ensuring alignment on strategy. For this reason, I am a strong advocate for holding regular town hall meetings with my company, both in-person and virtually. I communicate on three topics:

1. Where we are now
2. Where we are going
3. How we will get there

Additionally, I take questions from attendees at the town hall and answer them honestly and to the best of my ability.

I have been and am today the CEO of private equity-sponsored companies. When I take charge of a company, I do so with a mandate to increase its value, which usually requires turning the business around. By definition, this means that many of the puzzle pieces are missing. Doesn’t matter. You don’t need all the pieces to know what to do. The most important step is to share with the organization what you know right now concerning the where, what, and how topics I just mentioned. 

Level with the people of your business, revealing the good, the bad, and the ugly. Then, tell them how you and they together will make the necessary changes. I outline my four-step program.  

1. Step 1 is to set a goal. 
2. Step 2 is to frame a strategy. 
3. Step 3 is to build the structure that will support that strategy. 
4. Step 4 is to launch an appropriate action plan. 

The key to all this, when I come into an underperforming company, is to complete all four steps within 100 days. This does not mean finding all the missing pieces. This certainly does not mean achieving perfection. We will define the tactics and efforts required to execute the plan. We’ll make sound, informed decisions and go.

Going forward from this point, I augment the Four Steps with what I call The Four Commandments:

1. Be on pace.
2. Produce no surprises.
3. Be data-driven.
4. Believe that results matter.

These are the fundamental principles of effective, cohesive, and well-aligned strategic execution.

3.“In crisis situations, waiting for perfect data can lead to inaction. How do you balance the need for data with the urgency to make decisions, and how do you encourage teams to act decisively when time is critical?”

Some businesspeople are turned off by military metaphors and models. Me? I find them useful. Perhaps it’s because I'm a U.S. Navy veteran. Maybe it’s because both military and business leaders deal in highly dynamic situations involving high stakes. 

Concerning waiting for “perfect data” or perfection of any kind, the most successful commander of World War II, General George S. Patton, wrote: “The best is the enemy of the good. By this, I mean that a good plan violently executed now is better than a perfect plan next week. War is a very simple thing, and the determining characteristics are self-confidence, speed, and audacity. None of these things can ever be perfect, but they can be good.”

Look, common sense tells you that if your house is on fire, put out the flames, and if your boat is sinking, plug the leaks. Most business scenarios are less obviously existential, however, and another military figure had a good rule of thumb for determining when, whether, and how to respond. 

In 1954, when General Dwight D. Eisenhower was President Eisenhower, he explained his quick-and-dirty prioritizing framework: “I have two kinds of problems,” he said, “the urgent and the important. The urgent are not important, and the important are never urgent.” Steven Covey borrowed this and turned it into the so-called Eisenhower Matrix. You can look it up, but here’s the gist. 

There are four categories of situations:

1. The Urgent and Important are crises and deadline-driven projects that demand to be managed now. 
2. The Not Urgent and Important are situations and tasks that, while impactful, are not deadline-driven. These deserve focus. 
3. The Urgent and Not Important are tasks and situations that are time-defined but not of significant consequence. The proper response to these is to avoid responding. 
4. Finally, there is the Not Important and Not Urgent, which encompasses busy work and trivia of all kinds. Such time sucks are also to be avoided.

A crisis, or, in some cases, an opportunity, demands urgent (timely) action. Let yourself be inspired by Patton and act now in the knowledge that inaction in situations that are both urgent and important will almost certainly cause more harm than acting from incomplete data. 

You cannot modify or improve inaction, but you can review and modify action. Make no decision, and you abandon yourself and your organization to fate, chaos, or the hands of others. Make the wrong decision, and you can correct it with the right decision based on the data gathered directly from your own errors.

4.“Tough conversations about underperformance are often avoided, but you suggest they are crucial for a successful turnaround. What advice do you have for leaders who struggle with initiating these difficult discussions?”

As a leader, you must treat everyone fairly and respectfully. That is non-negotiable. However, you are not a parent, spouse, sibling, or buddy to your employees. As employees, they are allocated ownership of and accountability for what should be a clearly defined level of performance in clearly defined tasks, projects, departments, and functions. 

When employees fall short of that level, they must be advised, counseled, coached, and perhaps given further training. Management owns and is accountable for taking these corrective actions. It is quite likely that they will have a positive result, and you will, therefore, have no occasion for what can indeed be a painful conversation.

Not everyone succeeds, however. Not everyone can deliver the level of performance and productivity required, even after coaching and training. In this case, a conversation about underperformance is necessary.

“Fixing” people is not a leader’s job, which is a good thing because people can’t be “fixed.” Their behavior, performance, and output can often be improved. In business, it is always better to measure only what can be improved. Focus the conversation on performance. To the degree that you can objectively quantify output, do so and focus on it. Do not deliver a personality assessment. Do not scold. Do not berate. But do not apologize. 

Instead, define the level and nature of the results you and the community—the stakeholders in the business, including customers—expect. Offer help if you believe it will be helpful and of strategic value. Agree on a period within which the defined improvement must be achieved. If you and the employee are unable to agree on the terms, treat this outcome as you would any other negotiation that fails to reach a close. It is a business decision, and you are accountable to all stakeholders. Like the underperforming team member, they have feelings, too. Besides, there are more of them.

5.“You advocate for focusing on the 20% of efforts that drive 80% of results. Can you share an example where applying this principle transformed a team’s performance or helped simplify a complex situation? How do you help someone prioritize the right 20% when they’re overwhelmed with demands from all sides?”

Focusing on the 20% of efforts that drive 80% of results is not my idea; it is a law of nature, which was discovered by the Italian sociologist, political scientist, economist, and gardener Vilfredo Federico Damaso Pareto (1848-1923). He grew his own vegetables, including peas, which he tended lovingly and observed closely. 

He was struck by the fact that only a minority of his pea plants produced viable peapods. Since he was an economist, he ran the numbers and discovered that roughly 20% of his plants were responsible for 80% of his peapods season after season. This ratio stuck in his craw, and he began examining a wide variety of other phenomena to see if 80/20 was operative elsewhere in the world.  He found that the 80/20 ratio governing his pea plants applied to everything from the distribution of wealth and land among the people of Italy to Italian industrial output and, in fact, to practically every system or process whose input and output could be quantified.

Virtually every management decision we make is influenced or even governed by this natural law, which some call the Law of the Critical Few and the Trivial Many. Managers or leaders looking to understand and improve their business should study 80/20. Run the numbers on your own business, and you will find that roughly 80% of what you accomplish comes from just 20% of the time you spend working at it. 

The converse is also true: some 80% of your input of time and effort has a relatively trivial result, producing just 20% of measurable productivity. Fortunately, once you become aware of this disproportionate distribution, you can take proactive advantage of it. Using 80/20 analysis, you can identify the critical 20% versus the trivial 80% and reallocate your precious resources to overserve the 20% to thereby increase both gross margin and profit. 

This same analysis will also enable you to more strategically allocate resources to the lower 80% of your customers and products, resulting in much improved growth there. It will also guide you in shedding your lowest-performing customers and products. (Some customers are good to lose.) 80/20 is also a valuable lens through which to measure the productivity of your workforce and make assignments and other strategic personnel decisions accordingly.

6. In your experience, why do so many leaders fail to set a clear vision in their first 100 days, even though they know how important it is? Is there a deeper fear or hesitation at play?

I’ve never met a leader who didn’t want to succeed. But in my experience, many are more afraid of failing than they are driven to win. That fear can lead them to default to what they call the “long game”—chasing perfection, which they argue takes time. The problem? Struggling businesses don’t have time. And perfect companies? I’ve yet to see one.

Many leaders are fixated on building something “great”—something that lasts. They draw inspiration from books like Good to Great and Built to Last, aiming for legacy. But when you're trying to turn around a company, you don’t have the luxury of decades. The leadership culture I come from—private equity—is built around a different model: build to improve, build to grow, build to sell. Fast. It’s not about neglecting long-term value; it’s about focusing on what you can measure and move now.

That doesn’t mean every CEO needs to sell their company. But thinking about your business as a product—as something you can make more valuable over a clear time frame—sharpens your thinking. In private equity, that typically means tripling the value over five years. That’s the mindset: start strong in the first 100 days and drive toward measurable impact over five years.

Samuel Johnson said, “When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully.” The same applies here. Thinking with that kind of urgency brings clarity, focus, and momentum—and that’s how companies grow.

7. “It sounds like the first 100 days can make or break a leader. Is it possible to truly recover from these mistakes if they happen early on, or do they permanently hinder a leader’s effectiveness?”

I suppose the first 100 days could break a leader, but there is much more opportunity in this concentrated span than liability. There are two reasons for this: 1) The opportunity to make a big impact is significant. It invites the leader to lead with energy and audacity. If the company is in desperate straits, leadership has the confidence-building advantage of knowing that nobody ever fell out of a basement. 2) The second advantage of the first 100 days is that yes, it is possible to recover from mistakes made early on—for the very reason that they were made early on. Time is on your side.

Your first 100 days set the trajectory. Bill Canady’s advice boils down to a simple truth: action beats perfection every time. Whether it’s confronting tough conversations head-on, zeroing in on the critical few tasks that yield big results, or rallying your team behind a clear vision, the choices you make early shape your legacy as a leader. 

Check out the 'First 100-days Checklist,' and subscribe to The CTO Club’s newsletter for more insights!