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Ep #9: How to Wow When Asked About Your First 90-Days Plan

Mastering The Power Skills with Kathy Dockry | How to Wow When Asked About Your First 90-Days Plan

It’s September, and many of us are thinking about new beginnings. And when you’re facing a new beginning in your career…whether you’re in the running for a promotion, about to head a new project within your company, or starting afresh in a new organization…there’s one question you often get asked

The question is this: what’s your plan for the first 90 days? You could just give the same textbook answer everyone else does, but wouldn’t you want to wow people instead? You want to get off to a good start with everyone excited and enthusiastic about what you’re about to contribute to the organization.

Listen in this week to discover how to wow when asked about your first 90-days plan. Learn how to demonstrate your strategic thinking when posed this question, why listing off action steps often won’t wow in the way you might think, and Kathy’s top five tips for taking your answer to this question from acceptable to wow-worthy.


We’re celebrating the launch of the podcast here, and I’d like to include you. We’re going to be giving away AirPods Pros to five lucky listeners who follow, rate, and review the show. Today, September 13, 2022, is the last day so find out how you can enter here!


What You’ll Learn from this Episode:

  • Why you want to avoid answering the question of what you’re going to do in the first 90 days with a list of actions. 
  • Why you want to demonstrate your strategic thinking when asked about your first 90-days plan.
  • How to look head and shoulders above any of the other candidates for the role you’re after.
  • Why 90 days is actually too short a timeframe to display a meaningful contribution. 
  • 5 tips for wowing when asked about your first 90-days plan. 

Listen to the Full Episode:


Featured on the Show:

Full Episode Transcript:


Hi, everyone! Today we’re going to talk about a common situation where a subtle use of the power skill of persuasion can take your answer from good to great.


We’re airing this episode as the summer ends, and the back-to-school month of September is well underway. That got me thinking of new beginnings, and specifically a question that you sometimes have to answer when you are facing a new beginning in your career.


You might be in the running for a promotion or to head a new project in your organization, for example. Or you might be a candidate for a great job in a completely different organization.

Whatever the context, you’re likely to face this question several times in your career, and it’s always a good idea to wow people with your answer. You want to get off to a good start with everyone excited and enthusiastic about what you will do in the role.


So, what is the question that gets asked?


It’s this: “What is your plan for your first 90 days?” Or sometimes it’s another variation, like “What is your plan for your first year?” or a similar question.


However prepared you are to answer that question…and because most listeners to this podcast are highly motivated leaders, I assume you’re very likely to be prepared. But you may be missing an opportunity to wow people.


That’s because we take this question very literally and start to list the actions we are going to take in our first 3 months in the role. Of course, we do, because that’s what the questioner wants, right?


Well, no. It’s actually not what the questioner wants. And that’s a pretty definitive “no” by the way.

Whether the questioner is conscious of it or not, what he or she wants is reassurance, not a list of activities.


So, what does reassurance look like? It looks like you have a well-grounded strategy for how much value you’re going to add, approximately when you’re going to add it, and the means by which you’ll get there.


That’s different from a list of actions. When you answer this question with a list of actions, you give a sense of activity and busyness. But you don’t give strong reassurance that all that busyness results in any value.


The “first 90 days” question is an unintentional trick question. The person who asks it thinks that the list of actions is the information he or she needs, but it really isn’t.


So, no matter how detailed your response, he or she will still continue to have that need to feel reassured—to be wowed and completely confident that you will be a success in the role. And you haven’t yet met that need.


If that’s the case, then what is a really great answer to this question….an answer that will make you shine and look head and shoulders above any of the other candidates for the role? Well, of course, you know I have you covered on that, right?! Here are 5 easy, but really powerful tips that will get you there.


Tip #1: Don’t accept too short a time frame.


One of the reasons why the “first 90 days” question is so problematic is that it creates an artificial time frame. In the average organization, 90 days is too short a period to add any meaningful value.


People may like and respect you by that time. And you may have built a foundation for adding value in the future. But if you limit yourself to talking about your first 90 days, you’ll find it hard to talk about value at all.


Michael Watkins’ book The First 90 Days (which is where this all started) was a great contribution to management thinking on how to do a better job with onboarding. It’s a checklist approach to a topic (i.e., onboarding) that really benefits from having a checklist.


But the title Watkins used was a catchy one, and since his book was published many years ago, the title has now been taken as a catchphrase for a wide variety of topics where success depends less on having a checklist and more on having a

strategy. And when that new role you’re in the running for is a leadership role, then you really want to be demonstrating your strategic thinking.


A much better time frame to describe how you would approach a role is one year. A year generally gives you the chance to make a meaningful contribution, even if you’re still early in the role.


The only exception I can think of to that time frame is if you’re being asked about leading a significant project. Then you might consider a time frame more closely aligned to one of the major milestones for the project.


So, when you get asked what you plan to do in your first 90 days, how do you indicate that you prefer to change the time frame?


Simply say, “I always find that what I do in the first 90 days is highly dependent on what I’m targeting to accomplish in the first year. So let me start there.” I’ve never seen anyone have a problem with that response, so don’t be nervous about using it.



Tip #2: Talk about having a roadmap vs a plan.


One of the problems with using the word “plan” is that it can box you in. A year is a long time, and lots of unexpected things can happen when you’re in a new role.


If you’re not yet in the role, and you’ve set the expectation that you have a highly structured plan, what happens when you’re one month into the job and have run into an unexpected challenge?


You either have to scramble to meet the expectations that you’ve set, or you have a lot of explaining to do as to why you are suddenly behind in your plan. That’s not a good look during a time when people are still making up their minds as to how they think about you.


On the other hand, I’m sure you agree that you should enter the role with a good sense of direction and a goal as to where you want to be in a year’s time. So, what’s a good way to describe that to other people so that they are reassured that you won’t just be winging it?


Call your strategy a “roadmap” vs a “plan.”

Let’s talk about why the concept of a roadmap works. Think about getting ready for an extended road trip. You know where you’re starting, where you want to go, and when you want to get there.


The map helps you form a point of view as to which route you’ll take, the major destinations along your route, and perhaps how much ground you’ll cover each day.


But if any unexpected detours happen or a flat tire occurs, you’re not boxed in to keeping your route. You have options. You might cut down on some of the interesting side trips, or increase your mileage, for example.


The same concept holds true for your first year in a new role. Your best approach is to have a good sense of purpose and direction and the major milestones along the way.


But you also want to have the flexibility to deal smoothly and effectively with any unexpected challenges along the way. After all, you’re not in the role yet, and you haven’t gotten the lay of the land. It would be too unrealistic and even naïve to assume that you know everything, so you need that flexibility.

Talking about the roadmap for your first year shows that you’re a good navigator, one who thinks in terms of strategy. Simply tell your questioner that until you’re actually in the role, you prefer to describe your “roadmap” vs your “plan” and explain why the two are different. You’ll impress the questioner with your insight as to how the two are different.


Tip #3: Start at the end, not the beginning.


Starting at the end vs the beginning is a great approach not only for your answer, but for your own planning for the role. Why is that the case?


Well, if we continue to use the road trip analogy, you don’t plan an extended road trip without having an endpoint in mind. And once you have that endpoint, it’s so much easier to figure out how to get there by reverse engineering your route…saying to yourself something like, “If I need to get from NYC to San Francisco in 5 days, I need to get to Las Vegas by Day 4 and Denver by Day 3.”


So, starting at the end of the first year, figuring out what you want to have accomplished by then, and then determining the major milestones along the way is a very effective way of planning your first year.

However, taking that approach is also a very compelling way to frame your answer to the 90-day question.


Studies in linguistics show that when you talk first about where you want to end up, listeners perceive you as being more strategic and leaderly that they would if you start with Day 1.


Day 1 is important of course, and I’m not suggesting you ignore that. But don’t start there when you provide your answer.


Instead say something like, “Well, as I think about where I want to be at the end of year 1 in the role, I’d like to be able to make some detailed, actionable recommendations to the management team on long-term ways my division could be adding strategic value.”


Working back from that, I would need to have explored the following three areas by Month 9. So that means by Month 6, my team and I will have had to have gathered the preliminary analytics.” Etc, etc.


You can fill in this timeline however you want, of course. Just remember, that in talking about your roadmap for your first year, start at the end.

Tip 4: Categorize your first year into phases and give them names.


If you listen to this podcast regularly, you’re going to hear me repeat certain mantras regularly. One of them is this: It’s our job as leaders to make it easy for other people to understand us.


I’m going to say that again: It’s our job as leaders to make it easy for people to understand us.


This is closely related to another well-known rule of leadership that you may have already heard. Leaders are supposed to make the complex simple. The reason that both these statements are so important is this…people can’t follow you or support your ideas unless they understand you.


So, going back to your roadmap for your first year in a new role, how can you help people understand you when you’re throwing a lot of information their way?


You can do that by categorizing your year into a few phases and give those phases names or a short description.


Here’s an example of what one of my recent clients did when she was interviewing for a C-suite position in a new organization. She divided the year into 3 phases and described her roadmap as follows.


Phase 1 was a period of deep learning and listening. The day-to-day work already in progress would of course get done. But her main focus was going to be getting to know all important stakeholders and constituencies (including of course her team) and to develop a preliminary point of view on things like priorities and next steps, culture, personalities and work styles.


She called this simply the Learning Phase and told the new organization that she expected it to last 3-4 months.


Phase 2 was the time period where she would roll out a plan to address some of the priorities and low-hanging fruit that she identified during the Learning Phase. This would mean engaging more deeply with important stakeholders and constituencies. She would also be deepening her relationship with her team.


Were the division structure and roles optimized for success going forward? What support or leadership development did they need? She called this period the Quick Wins Phase and told the new organization that she expected that phase to last approximately 6 months.


Phase 3 was the period where she and her team would start designing and refining a longer-term plan for the division. She intended to run parts of the plan by key stakeholders during this phase to get their insight and input.


Finally, she would present the plan to the CEO and management team to get alignment and approval. She called this phase the Long-Term Strategy Phase, and she told the organization that she expected it to last approximately 3 months.


Now of course my client gave even more detail in her answer than I’ve given you here. But notice what she did in taking this approach.


She knew that after a lengthy interview, the questioner could easily forget some of the details she provided or even get them confused. However, the questioner was highly unlikely to forget the named phases: the Learning Phase, the Quick Wins phase, and the Long-Term Strategy Phase.


That means her answer was “sticky.” It was framed in a way that would stick in the minds of others and as a result, it could be easily remembered.  Her answer provided assurance that she knew where she was going and had a clear strategy to get there.


So, before you get asked the “first 90-day” question, think about what phases are appropriate for your year and think about what names you would give them.


And finally, Tip # 5? Be sure to specify particular milestones where you will report back to your boss or key decision makers.


While companies love organized leaders with a firm sense of direction, they also have been burnt by new leaders who go charging off without having regular check-ins with their boss.


You know that person…the one who calls himself a change agent and then mows everyone else down? Now I know you wouldn’t be that person. However, you can pretty much count on that worry being in the back of your questioner’s mind.


So, make a point of explicitly removing that doubt. Indicate key moments in your first year when you plan to check in with your boss on how things are going.


You’ll want to update him or her on your insights and observations, describe what you intend to do during the next phase of your year, and get valuable feedback and guidance. The purpose of doing this is to ensure you are aligned around important factors like priorities, pace and communication.


And by the end of the year, be sure to plan on reporting back to other key decision makers – perhaps your boss’s boss or the management team or even the board. Remember, the end of the year is when you’ll likely be making recommendations on your long-term strategic plan, so it will be important to ensure all your constituencies are aware of that and on the same page.


Just spell this all out in your answer, and your questioner will be impressed with how you’re already thinking about how best to communicate and keep aligned with the team.


OK, there you have it…5 tips that will take your answer to the “first 90-day” question from merely acceptable to truly wow-worthy. Make it easy for decision makers to understand what value you can deliver, and in turn they’ll also find it easy to see why you’re the right person for the role.


Now before we close out today’s episode, I want to be sure you know about some other resources we have available to you if you’re considering a new role whether within your company or outside it. These are all resources that will either give you a competitive edge or help you avoid some of the common mistakes that others make.


First, last week’s episode was entitled “3 Tips For Landing A Good-Fit Job,” and I shared 3 highly effective but little-known tips that will help you create a great impression when you want to land that role that’s a great fit for you.


You can listen to that episode, of course. But I’ve also put these tips in a simple infographic for you, so you can file it away and retrieve it in the future when you might need it. You can grab a copy of that infographic for yourself by clicking the link in the show notes for this episode.


And if you want to have some more inside tips to put in that file, you may want a copy of our latest free white paper “3 Mistakes To Avoid When You Want A Role That You Can Thrive In.”


I wrote this paper after I started noticing leaders ending up in bad-fit roles. They thought that they had found their dream jobs, but instead they ended up in companies where the culture or the personalities were a bad fit.


That’s a pretty demoralizing situation to be in, and it’s one that seems to be increasing as the job market becomes more active. When I saw that, I wanted to be sure my clients and audience are never in that position.


The “3 Mistakes To Avoid” paper will give you insight on these common mistakes and guide you to solutions that increase the odds that you are attracting only good-fit roles. We’ll include a link to that paper as well in the show notes.


Finally, several times a year, we offer an online digital course where I walk you through a step-by-step strategy for attracting good-fit roles. We’re offering that course soon. If you check the show notes for this episode, you’ll find a link that will give you more information on that and the ability to sign up.


I highly encourage you to check that out. This is the same strategy that many of my senior management clients have used not only to their dream opportunities, but to show up as compelling and confident as they navigate their way to an offer.

You’ll learn all sorts of power skills that will serve you well in today’s job market. And if you’re listening to this episode at a later point in time, don’t worry that you’ve missed out. If you click the link in the show notes, you’ll get added to the waiting list, and we’ll alert you when the course gets offered again.


Well, all right, my friends – here’s to all those resources supporting you as you take your careers to the next level! I hope you have an awesome week ahead, and I look forward to seeing you in our next episode!


We’re celebrating the launch of the podcast here, and I’d like to include you.

I’m going to be giving away AirPods Pro to five lucky listeners who follow, rate, and review the show. Now, of course, you don’t have to give the show five stars, although that would be awesome and I do hope you love what you’ve heard so far. But I’d also love your honest opinion and feedback as well as your questions so I can create a show that’s a valuable resource for you.


So visit to learn more about the contest and how to enter and I’ll be announcing the winners on the show in an upcoming episode.


Thanks for listening to this episode of Mastering The Power Skills. If you like what was offered in today’s show and want more insights and resources from Kathy, check us out at


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About the author

Kathy Dockry is the Managing Director of Significa Group LLC. Our clients are CEO’s, senior management executives, functional leaders, and fast-rising high potentials in complex organizations. Significa helps them hone the leadership, influence and navigational skills that takes their career success to new levels and brings meaningful change to their organizations.