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:
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:
Advice for a 100 day new leader plan: “Build relationships with your team”, “Deliver some quick wins”, “Identify strategic priorities”. No s^^t, Sherlock!
Time for a new approach:
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?
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?
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.
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!):
Before day 0: CHOOSE A WINNABLE GAME
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.
Day 0: PREPARE FOR TAKEOFF
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’.
Day 1: BE THE MANIFESTO
Your first day sends huge messages. Get it right with this one critical question.
Days 2-30.: 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. 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
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?
You really want to know this before you start. You don’t want to get on a ship that’s already sunk! These follow-up questions can help you dig deeper (1):
Q2. Does the organisation’s Readiness To Change match their Need To Change?
This question goes hand in hand with the previous one.
Because the lack of winning strategy might not be a problem, if the organisation is ready and willing to do what it needs to change.
If you’re a turnaround expert AND the organisation is aware of its need to urgently make significant changes, that’s one thing - but otherwise you are setting yourself up for failure from the outset.
Q3. How will I know if I’ve been successful - and what resources do I have to do the job?
Many leadership roles are effectively impossible from the start because of unrealistic or conflicting expectations among key stakeholders. Speak with your key stakeholders and listen carefully for contradictions, uncertainty or signs of internal friction.
Specifically, find out what each stakeholder understands as regards your (1) role and responsibilities, (2) goals and timeframe, (3) authority, (4) access to essential resources.
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?
This gets at the tricky question of personal fit. You need to be ruthless about your motivation, your skill set and your cultural match - otherwise you and your employer will be both heading for a rude awakening in a few months time.
For example, I’ve seen a number of cases where a VP at a tech giant has jumped into a CXO role in a hot new startup - only to be shocked and disillusioned at the lack of resources and the amount of ‘rolling up their sleeves’ that’s necessary in the new environment.
"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."
- Thoughts on new leader 100 day plans from Pierre-Antoine Vacheron (CEO, Natixis Payments)
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:
Q5. What are the key priorities that you see?
Get a sense of what your stakeholders see as the critical issues. Remember, this is a listening and rapport exercise. With senior stakeholders, you’re looking for direction. With peers, you’re building mutual understanding. With your own reports, you want to learn about their reality and needs.
Q6. How would you prefer we communicate?
Now’s a great time to start to map out your communications plan, so ask about their communication preferences: their idea of what the best manner (email, call, coffee/chat,…) and frequency would be, and how they would prefer you to handle disagreements (for example: no holds barred, tell me privately, never ever disagree with me,…).
Q7. What do I need to know about how decisions get made?
Ask about the decision-making process, control points and vetos, who to keep in the loop, personalities to be aware of, and so forth.
Q8. How am I likely to sabotage my own success?
This is a question to be asking yourself during this period. You have a fantastic opportunity to “up your game” and play at a higher level, so think about your tendencies and consider how they are most likely to undermine you in the early months.
For example, introverts might have a tendency to under-communicate; extraverts to fail to listen deeply and to pick up on subtle warnings. Visionaries might tend to frustrate operationally-minded folk with vague inspirational speeches, and more hands-on leaders may fail to step back from immediate operational requirements to develop fresh new strategies.
Identify one or two key tendencies to be aware of.
Q9. What’s my leadership message?
This is the other question to be asking yourself during this period. You need to prepare a couple of ready-to-go speeches about who you are, why you’re here, what you believe in, and why people should listen to you. You’ll need to set some expectations from day one.
"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."
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?
First impressions count. A lot. So your first day on the job will be a crucial moment. Make the most of the insights you’ve gained in ‘day zero’ to structure your first day so that your actions speak just as loud as your words.
For example, if “listening to the customer” is a big part of your message, set things up so that you do just that on your very first day.
Bradt et al (1) suggest the following checklist as a good template to start with, but you’ll need to adapt it quite considerably to your situation:
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
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?
As you meet the most obvious stakeholders, get their view on the less obvious people to speak with. You’ll want to spend a good amount of time with people on the frontline of the business, such as salespeople and customers. But ask around for ideas.
Q12. What’s the festering wound?
As Boston Consulting Group say, “understand the problems that reside on the balance sheet and communicate them early. You get one chance to erase the mistakes of your predecessors. Identify and deal with these legacy issues immediately.
Unpleasant surprises—obsolete inventory, insufficient warranty reserves, excessive goodwill, unresolved customer disputes, and festering litigation—have a way of hiding behind the numbers.”
Q13. What’s the Rallying Cry?
Towards the end of the first 30 days it’s normally a good idea to bring your leadership team together to define the overall narrative of the business. This includes the high-level vision/mission, strategic anchors and key performance indicators (KPIs).
But most critical of all, this workshop needs to build agreement and clarity on the all-encapsulating phrase or tagline that defines the burning imperative in the business.
This is the rallying cry - the #1 priority for the organisation right now.
Once you have this in place, it becomes so much easier to communicate your vision of a better future and help employees understand how they can contribute to the new direction.
"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."
- Thoughts on new leader 100 day plans from Ashley Friedlein, CEO & Founder, Guild
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?
As you explore the business, keep a list of potential quick wins by asking as many people as possible this question.
You can then filter and prioritise. Bradt et al (1) give 6 helpful criteria for quick wins:
You’ll need to judge how many you can truly deliver “quickly”. Allocate enough resources, give the team responsible a clear charter, and celebrate and communicate on early successes (champion the champions!).
Q15. What’s holding your execution back?
Now’s also a good time to understand the bigger systematic issues that are holding your teams back. Organisational inefficiencies in decision-making, unclear roles/responsibilities, linkages across groups, information flows and inadequate collaboration can all come into play. You need to start to understand which are annoyances and which are real roadblocks.
Q16. Who’s my core team?
You need to have your leadership team pretty much in place by day 60.
Sometimes you need to move faster, though there is a risk that you’ll make poor decisions and come across as too impulsive. But moving too slow is a greater risk.
After 100 days, the team will be seen as ‘your team’. The problem children become your problem children, and no longer the legacy of your predecessor. High performers will be frustrated if low performance is still being tolerated or ignored.
"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."
- Thoughts on new leader 100 day plans from Matthieu Stefani (CEO, CosaVostra)
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?
A consistent drumbeat of communication to all stakeholders - up, down and across - is something I see leaders struggle with on a regular basis. After the initial flurry of activity, good intentions can fade away around the 61-100 day period. Work with your leadership team to make sure that everyone - from your board of directors to the front line - is receiving consistent, relevant communication.
One of my Founder/CEO clients, Mike, was shocked during a workshop we were running to find that his management team didn’t know his strategic priorities. He believed he’d communicated incredibly clearly - but the reality was was very different. It was an ‘aha moment’ for him and made a big difference to how the team pulled together.
Q18. What ongoing rhythms do I need to put in place?
At around the 61-100 day period, it’s good to give some thought into the ongoing governance that will continue to drive your change initiatives forward. How are you going to ensure cross-team interlock? Solve strategic issues? Identify and resolve roadblocks on strategic projects? Periodically review and refine the organisational strategy?
Our experience is that separate meeting formats are needed for each of these aspects. Merging them into a general ‘management meeting’ is a recipe for the typical “meeting muddle” of updates, discussions, debate - but not a lot of strategic decision-making and bold moves forward.
In a future article I’ll cover this essential topic in a lot more detail, but for now the graphic above can give you a simple structure to follow.
"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."
- 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