30-60-90 Day Plan for Executives: The Ultimate Guide

Q1. Is there a 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. Is there a readiness to change?

The lack of a winning strategy might not be a problem if the organisation is ready and willing to do what it needs to change.  But if the readiness to change is not where it needs to be, you are setting yourself up for failure from the outset unless you are a seasoned turnaround expert.

Q3. What exactly does success look like?

Many leadership roles are a poisoned chalice from the start because of unrealistic or conflicting expectations among stakeholders. Speak with them and listen carefully for contradictions, uncertainty or signs of internal conflict. 

Q4. Do I have the resources to succeed?

Specifically, make sure you that you have the necessary, authority, timeframe, and access to resources to be able to deliver against the success criteria you established in question 3.

Q5. Why did you offer the role to me?

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 in a tech giant has jumped into a CXO role in a hot start-up or scale-up, only to be shocked at the lack of resources and the need to ‘roll up their sleeves’ in the new firm.

Q6. What priorities do you see?

Get a sense of what your stakeholders see as the most important opportunities and challenges to address. This is a listening and rapport exercise. You're looking for direction from senior stakeholders, for mutual understanding with peers, and for an understanding of the needs and issues facing your own reports.

 Q7. How would you prefer we communicate?

Ask your stakeholders about how they would prefer to communicate: medium (email, call, coffee/chat,…), frequency, and how they prefer you to handle disagreements (for example: no-holds barred, discuss privately, or never, EVER, disagree with me!).

 Q8. What do I need to know about decision-making?

Ask how decisions get made.  Shaping decisions is going to be a key part of your 30-60-90 day plan, so find out about process, control points and vetos, who to keep in the loop, personalities to be aware of, and so on.

 Q9. How might I sabotage my own success?

This is a question to be asking yourself during this period. It's a great moment to reinvent yourself, up your game and play at a higher level, so consider how your default patterns of behaviour are most likely to undermine you in the early months.

By way of example, you might have a tendency to under-communicate (if you're an introvert), fail to listen deeply (if you're an extravert), frustrate operationally-minded folk with vague inspirational speeches (if you're a visionary), or fail to step back from immediate operational requirements to develop fresh new strategies (if you're a hands-on leader).

Identify one or two key tendencies to be aware of.

 Q10. What’s my leadership message?

This is the second question to be asking yourself during this 'day 0' period of your 30-60-60 day plan for executives.

Start preparing a ready-to-go message 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.

Q11. How will my first day communicate the values and the tone I want to set for the business?

Your first day on the job will be a crucial moment, and you have the opportunity to make the most of the insights you’ve gained in the previous phases to structure your day so your actions speak as loud as your words.

For example, if you have built a message around “listening to the customer", then set things up so that you do just that on your very first day.  If your message is that people are the most important part of the business, then how will you demonstrate that?

This checklist (from Bradt et al (1)) might give you a good first draft to work from:

Q12. Who should I be speaking to? Who'd 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.

 Q13. What is the festering wound that needs attention?

“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.” As Boston Consulting Group.

 Q14. What’s the Rallying Cry?

Towards the end of the first 30 days you will probably want to bring your leadership team together to define the overall narrative of the business. This includes your purpose, your stakeholder expectations, your strategic anchors and definition of success

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.

We call this "the rallying cry" - the #1 priority for the organisation right now.

Once you have this rallying cry dialled in, it becomes so much easier to communicate your vision of a better future and help the wider team understand how they can contribute to the new strategy.

Q15. 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 these helpful filters for quick wins:

You’ll need to judge how many you can truly deliver “quickly”. Better to deliver a few projects quickly and well, than overpromise and underdeliver. Allocate enough resources, give the team responsible a clear charter, and celebrate and communicate on early successes (champion the champions!).

 Q16. What’s holding back execution?

Now’s also a good time to understand the bigger systemic issues that are holding your teams back. These might include:

You will need to start to determine which are annoyances and which are real roadblocks.

 Q17. Who’s my trusted team?

You will 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 leaders become your responsibility now, and are no longer the legacy of your predecessor. And the high performers will be frustrated if low performance is still being tolerated or ignored.

Q18. Am I communicating clearly & consistently?

A consistent cadence of communication to all stakeholders - up, down and across - is something leaders struggle with on a regular basis.

After the initial flurry of activity, good intentions can fade away around the 61-90 day period.

Instead, work with your leadership team to make sure that everyone - from your board of directors to the front line - is receiving consistent, clear and concise communication.

One of my Founder/CEO clients, Mike, was surprised to find out during a workshop that his management team really weren't clear on his strategic priorities. He believed he’d communicated incredibly carefully - 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.

Q19. What ongoing rhythms do we need to install?

At around the 61-90 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 alignment?
• Solve strategic issues?
• Identify and resolve obstacles on strategic projects?
• Periodically refine the organisational strategy?

Our experience is that separate meeting formats are needed for each of these aspects. A single 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.