November 19


The New Leader’s 100 Day Plan

18 powerful questions you need to ask

If you’re taking on a new leadership role, your first 100 days are critical. As you’ll be aware, the stakes - for you and your organisation - are high. Check out this graphic from McKinsey, a consultancy:

New leader 100 day plan - McKinsey

As you can see, 90% of leaders who had a successful transition deliver on their three-year performance goals. But when leaders struggle through a transition, the performance of their direct reports is 15 percent lower than it would be with high-performing leaders.

The problem with most advice on 100 Day Plans

The idea of a new leader 100-day plan is common. There are plenty of articles and books on the topic. Whilst I’ve benefited from these myself, they tend to fall down in two ways:


  • They can be incredibly detailed and long. It’s like operating a computer with an enormous ring-bound user manual at your side. Great as a reference tome, but hardly as a day-to-day guide.
  • The shorter articles can be incredibly vague. “Build relationships with your team”, “Deliver some quick wins”, “Identify strategic priorities”. No s^^t, Sherlock!

Advice for a 100 day new leader plan: “Build relationships with your team”, “Deliver some quick wins”, “Identify strategic priorities”. No s^^t, Sherlock!

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Time for a new approach:

  • Wouldn’t it be great if you had a one-page roadmap, a simple list of powerful questions to be answering during this critical 100 day period as a new leader?
  • You’d be able to print it out, carry it with you, jot down thoughts against each question, see where you’re coming up short of answers, and be able to course correct as you go.
  • Even better, the questions would be organised by month, so you don’t have to be looking at all the questions all the time.

Guess what? It’s your lucky day. This article covers 18 powerful questions you should be asking in the first 100 days of a new leadership role. You can also download a one-page PDF “cheat sheet” for simple reference by clicking the link below.

Is a New Leader 100 Day Plan truly necessary?

Whilst some books and analysts certainly overplay the importance of 100 days (research suggests the reality is investors will give CEOs 8 months to articulate a strategic vision and almost 2 years to turn a company around), it’s important to build credibility and momentum early.

Avoid common mistakes: Korn Ferry researched leaders in Americas, Europe, and Asia and identified the common mistakes that senior executives make during their first 100 days. Which of the top five is the mistake you’re most likely to make?

  • Failing to establish strategic priorities - 24%
  • Committing cultural gaffes and/or political suicide - 16%
  • Waiting too long to implement change - 16%
  • Not spending enough face time with subordinates - 14%
  • Getting sidetracked by “fire drills” — having a short-term focus - 11%

Design for success: Korn Ferry also surveyed the #1 thing — above all else — that a senior executive must build into their new leader 100 day plan to succeed. Which of these is most likely to be your blindspot?

  • Assemble and solidify a team - 25%
  • Articulate a statement of vision and goals - 25%
  • Identify and address what’s most important to the CEO, board of directors and other key executives - 16%
  • Understand and adapt to the new culture - 14%
  • Identify the leverage points and the metrics for success - 10%

Boston Consulting Group (2) asked 20 CEOs for their top advice about the first 100 days in position. Here are some of the key quotes:

“Diagnose first, decide second.”

“Follow your instincts.”

“Take notes, then prioritise and act.”

“Understand that as the head person, you have only three topics: people, strategy, and values. Everything else is secondary.”

“Find people you trust and use them for problem solving.”

Finally, Harvard Business Review surveyed executives to find the biggest errors and pitfalls in the first 100 days that impacted their ability to deliver the results they wanted.

HBR new leader plan pitfalls

Action Point: In summary: you need to be on your A-game at this period. There are a lot of moving parts, and change once for one to get this right.

New Leader 100 Day Plan: Overall Roadmap

There are 6 phases you need to be thinking through, and there are specific questions for each. You’ll notice that the first two or three of these are typically forgotten about by new leaders (at their peril!):

Overall Roadmap

Before you accept the role, there’s some due diligence you absolutely need to do. Use these 3 questions to make sure your new leadership position isn’t doomed from the start.

This is the period between accepting the offer and turning up for the first day on the job. Most leaders fail to take advantage of this unique season. But you, high performer, are different, and will use the time to develop some relationships and perspectives prior to arrival. Here are the questions you need to be asking during this period, sometimes called the ‘fuzzy front end’.

Your first day sends huge messages. Get it right with this one critical question.

The first month of your new leader 100 day plan is about understanding the people and the issues, and validating your #1 strategic objective. Ask yourself these powerful questions to rock this phase!

Days 31-60: MAKE YOUR MOVE
The second month of your new leader 100 day plan is when you’re likely to make some major moves, in terms of people and projects. Here are 18 important questions to be asking.

Days 61-100: KEEP IT UP
The final period of your 100 day plan as a new leader is a mixture of execution and preparation for the longer term. Here are three questions you should not forget as the honeymoon period comes to a close.

So, with the overall roadmap in mind, we can jump in to the questions. But for a deeper understanding, I recommend you check out the box below:

The power of CONTEXT to frame CONTENT

A piece of information, in isolation, is very difficult for us humans to process and evaluate. We need to compare it to something else. Apples to apples, or oranges to oranges.

It’s this CONTEXT that allows us to assign a level of "value" to the new piece of information.

Say I was talking to you about, say, some new videoconferencing software. Consider the difference between:

  • “It’s so good you don’t need to spend $1000 on airfare each time you want to run a meeting. The software costs $50 per month.”
  • “It’s so good it’s a real step up from using Skype for free. The software costs $50 per month.”

Similarly, when I coach leaders I often suggest they invent a catchphrase. It’s a great way to change culture and spread their way of thinking within their organisation.

The thing about a catchphrase is it needs context. Otherwise people won’t notice.

Simply saying “we have a saying around here” opens up a context for what is now going to be said. The expectation is that some valuable piece of insight and shared wisdom is about to be shared, and people listen up and pay attention.

The power of using CONTEXT to shape in your new leadership role.

There are six distinct phases to a successful 100 Days as a new leader. The initial phases build context in a very specific way to make success way more likely. Indeed, one central phase is almost ALL about delivering a powerful context to the organisation.

Check out this quick (4 minute) video where I explain all:

New Leader 100 Day Plan: Before Day 0

New Leader 100 Day Plan: Before Day 0

The motto for this phase is CHOOSE A WINNABLE GAME. You need to do your due diligence BEFORE you accept the role (which is a great reason to forward this article to anyone you know considering a job offer).

Before you accept the offer, speak with a handful of stakeholders with varying perspectives, and ask them these questions to validate that your New Leader Plan has a good chance of succeeding.

Q1. Is there a clear, differentiating, and winning strategy?

Q2. Does the organisation’s Readiness To Change match their Need To Change?

Q3. How will I know if I’ve been successful - and what resources do I have to do the job?

Xavier, a new president, failed to consider reporting lines and resources, and soon learned that his only direct reports were the heads of sales and business development. Marketing, finance, information, or human resources did not report to him. By taking the title of president, but not having the appropriate authority, he’d set himself up for failure from day 1.

Q4. What, specifically, about me led you to offer me the job?

"I am personally very disciplined around the first 100 days. Spend massive time within the teams to get a grip on the business and the culture; assess top management; have a defined vision and first roadmap at the end of the period and communicate around it; get two to three concrete results to demonstrate momentum."

Pierre-Antoine Vacheron

- Thoughts on new leader 100 day plans from Pierre-Antoine Vacheron (CEO, Natixis Payments)

New Leader 100 Day Plan: Day 0

New Leader 100 Day Plan: Day 0

The motto for this phase is PREPARE FOR TAKEOFF. “Day 0” is not just one day of the new leader 100 day plan. It’s actually the period between your acceptance of the position and the first day on the role. Many leaders ignore this period entirely with the excuse they’re too busy wrapping up their previous role or taking a family break.

Big mistake. This “day 0” period is a fantastic time to prepare to hit the ground running and make an impression right on day 1. In day 0, you’ll be focusing on building a draft communication plan, learning plan and stakeholder map.

Let me say it clearly:

Contacting key stakeholders before you start will make a huge difference. It’s a game changer. If you do one thing from this entire article, do this!

A good checklist of people to contact would include:

  • Your new boss.
  • Key board members.
  • Critical peers.
  • Key customers.
  • Key direct reports.

Q5. What are the key priorities that you see?

Q6. How would you prefer we communicate?

Q7. What do I need to know about how decisions get made?

Q8. How am I likely to sabotage my own success?

Q9. What’s my leadership message?

"I’ve already reached out to some future colleagues and some agency counterparts just to introduce myself. You’re right—it is game changing. Everyone has reacted with warmth and candour, and it will make the first few weeks far more effective and enjoyable."

- Nathaniel

New Leader 100 Day Plan: Day 1

 New Leader 100 Day Plan: Day 1

The motto for this phase is BE THE MANIFESTO. Your first day sends huge messages. Here’s the one critical question to be asking.

Q10. How is my first day going to communicate my values and the tone I want to set for the organisation?

Karen was coming into a bank to merge three divisions into one. Each division manager had an off-site meeting already planned for her first two weeks, and she initially decided to use those as a chance to meet the key players. However, these individual divisional meetings perpetuated the culture of three different divisions as opposed to one combined group.

So to set a new course, Karen rented a theatre for Day One and invited the entire staff of each division. Then she introduced herself to the entire staff of the new division at the same time. She followed this with a social event designed to get the three divisions mingling. She eventually went to the old divisions’ off-sites, but only after setting the stage for the new, combined division.

"As a new leader you are absolutely sure to feel imposter syndrome. Fight it: you’ve earned this and I’m sure you’re here for a reason. Put your head down and do the work, you will succeed!"

- Thoughts on new leader 100 day plans from Gabriel Jarrosson (Founder, Leonis Investissement)

New Leader 100 Day Plan: Days 2-30

New Leader 100 Day Plan: Days 2-30

The motto for this phase is FIND THE RALLYING CRY. The first month of your new leader 100 day plan is about understanding the people and the issues, and validating your #1 strategic objective.

Q11. Who should I be speaking to? Who would you warn me against?

Q12. What’s the festering wound?

Q13. What’s the Rallying Cry?

"In your first 100 days don’t promise any answers. Promise to listen; promise to summarise and feed back what you learn; promise to use the time to come up with a considered plan that you can then be held to."

Ashley Friedlein

- Thoughts on new leader 100 day plans from Ashley Friedlein, CEO & Founder, Guild

New Leader 100 Day Plan: Days 31-60

New Leader 100 Day Plan: Days 31-60

The motto for this phase is MAKE YOUR MOVE. The second month of your new leader 100 day plan is when you’re likely to make some major moves, in terms of people and projects.

Q14. What’s one simple, inexpensive thing we could do?

Q15. What’s holding your execution back?

Q16. Who’s my core team?

"At first, meet as many people as possible, at any level. You need to understand how the business works, not just the C-Suite. Then look, feel, test and iterate. You're here to try new things, and not to change everything. Finally, find who are the best people you want to work with, and take your responsibilities: change what you want to change."

Matthieu Stefani

- Thoughts on new leader 100 day plans from Matthieu Stefani (CEO, CosaVostra)

New Leader 100 Day Plan: Days 61-100

New Leader 100 Day Plan: Days 61-100

The motto for this phase is KEEP IT UP. The final period of your new leader 100 day plan as a new leader is a mixture of execution and preparation for the longer term.

Q17. Am I communicating consistently?

Q18. What ongoing rhythms do I need to put in place?

"While boldly attempted by many, building a CEO platform of trust just doesn’t happen in 100 days. Instead focus on building the foundation. Trust is earned through transparency (what’s going well and not so well at the moment), care for your people (a true partnership in their development and involvement), and doing what you say you’re going to do."

Phil Saunders

- Thoughts on new leader 100 day plans from Phil Saunders (President & CEO, SABA Software)


If you’re taking on a new leadership role, these 18 questions for your first 100 days represent a powerful checklist to keep you thinking through all the bases in what’s likely to be a hectic time.

If you’d like to download the questions as a simple ‘cheat sheet’, then you can do so here.

Finally, I specialise in helping ambitious, competent leaders dramatically grow their impact and influence and achieve more than they could imagine. And if you’re starting a new role, that’s a perfect time to reinvent yourself and play a bigger game.

If you’d be interested in rolling up your sleeves and mapping out what the top 1-2 game-changing moves will be for you in your new role, you can apply for a complementary coaching session, with no obligation to buy or do anything.


(1) The New Leader’s 100 Day Action Plan; 2011; by George B. Bradt, Jayme A. Check, Jorge E. Pedraza; Wiley.

(2) Assuming Leadership: The first 100 days; 2003; Patrick Ducasse, Tom Lutz; Boston Consulting Group.

Successfully transitioning to new leadership roles; McKinsey & Co; 2018

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