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Ep #28: How To Wow Others When Asked About Your 90-Day Plan

Mastering The Power Skills with Kathy Dockry | How To Wow Others When Asked About Your 90-Day Plan

If you’ve ever had the experience of stepping into a new role or undertaking a major project, there’s one question that you’ve probably expected to get asked: what is your 90-day plan? 

It’s one that has become commonplace in the corporate playbook, and it’s likely that you’ve shown up ready with a game plan before you get asked. However, the truth is this question has now morphed into something that’s not all that helpful anymore. The corporate world is now a more sophisticated, nuanced place than it used to be, so how do you wow people with your answer?

Listen in this week to discover how to take your answer to the question of your first 90-day plan from acceptable to wow-worthy. You’ll hear five simple but powerful tips that will help you clarify the value you have to offer, and in turn, show other people the meaningful difference you can truly make. 


If you’d like some personal guidance on how to use the power skills of influence, persuasion, or presence in your workplace, we’ve got your back. Email us explaining your situation, and we’ll feature your inquiry on an upcoming episode, making sure you have tips and strategies to help navigate your situation skillfully.


What You’ll Learn from this Episode:

  • Why the 90-day plan is no longer a useful framework. 
  • The danger of answering the question of your 90-day plan with a list of actions. 
  • How you might be missing the opportunity to wow when asked about your 90-day plan.
  • What reassurance looks like. 
  • 5 easy but powerful tips to help you wow when asked about your 90-day plan.


Listen to the Full Episode:


Featured on the Show:

Full Episode Transcript:


You are listening to episode 28 of Mastering The Power Skills. When we step into a new role, whether through a promotion or by going to another company, we’re often asked about our plan for our first 90 days. The trouble with answering this question literally, however, is that you could end up sounding pretty tactical and humdrum. In this episode, I’ll provide you with a way of responding that will wow other people and make you look much more strategic.


How much more could you accomplish if you were 25% or even 50% more influential and persuasive? Welcome to Mastering The Power Skills, the podcast that provides you with tips, strategies, and the inspiration to grow your own power and win support for your ideas. And now here’s your host, C-suite leadership coach Kathy Dockry.


Hi, everyone. Well, it’s early February as we air this episode. And if you’re anything like my coaching clients, you may be about to undertake a new project or even a new role for the year. And if so, congratulations. It’s always exciting to show what you’re capable of and to be working towards something that can make a meaningful, positive difference.


All those new beginnings, though, got me thinking about a topic that we aired last year that really resonated with the audience. It was pretty popular, and I still get asked about it a lot. So we’re going to air it again in case you missed it the first time around. The topic is one that’s become part of the normal corporate playbook or corporate speak; it’s the first 90 days plan.


When we start a new role or lead a new major project, we’re all kind of expecting to get asked the question, what’s your 90-day plan? Nothing too unexpected about that, right? In fact, we’re usually putting together some sort of game plan before we get asked that question. It’s that common of a thing. But like a lot of traditions in corporate life, that whole 90-day concept started off as a helpful idea and has now morphed into something that isn’t always very helpful at all.


Several decades ago, there wasn’t a well-thought-through process for how to quickly and efficiently get up to speed in a new role or on a new project. Everyone tended to have their own favorite approach, and sometimes that was good, and sometimes it was problematic. Then along came Michael Watkins out of Harvard with a book called The 90-Day Plan. It became a best seller because it provided us all with some very useful checklists and best practices for getting up to speed.


It helped provide some needed structure and discipline that had been lacking in the corporate world. And it helped us all take our game to the next level. Now, cut to over, I think, 20 years later. The corporate world is a more sophisticated, nuanced place than it used to be 20 years ago. And concepts that were originally novel and hugely helpful are just part of what we already know. We’ve absorbed those concepts, and we really don’t need to follow them page by page.


The First 90 Days book is more a reference manual now than a bible. We just quickly scan it to see if there’s any item on the checklist that we may have overlooked. And you know, that whole concept that you have to be up to speed in 90 days, there was never any magic or real science around that number, and there still isn’t. We all instinctively know that the amount of time needed to get up to speed is very much linked to the circumstances of the new situation we’re taking on.


Sometimes the project requires us to move more quickly than 90 days, and sometimes the project makes it wiser to draw things out for longer than 90 days. It all depends on what the overall timeline is, how critical things are, and also how complex they are.


So, why am I telling you all this? Well, because even though we all know that 90 days is simply an arbitrary benchmark for our plan, it doesn’t prevent other people from asking us that question. The phrase is now just part of our shared corporate lingo. It’s just hanging around because it’s catchy. And it’s no longer a really useful question because it doesn’t get at what the questioner really wants to know.


The danger for you in answering that question literally by giving a list of tasks to be completed in 90 days is that you end up looking tactical and kind of mundane. You’re not answering what the questioner really wants to know. But, no need for you to worry about that anymore. This episode is all about how you can answer that question in a way that serves you well and impresses the questioner.


So let’s jump in right now and explore how you can wow people the next time you get asked this question.


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, 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. What you want is to get off to a good start, with everyone excited and enthusiastic about what you’re going to 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.


Now, however prepared you are to answer that question, you may be missing an opportunity to wow people with your answer. And that’s because we take this question very literally and start to list the actions we are going to take in our first three months in the role. Of course, we do that, right, because that’s what the questioner wants.


Except, 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’re giving 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 really 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, the questioner will still continue to have that need to be reassured, to be wowed, and completely confident that you’re going to be a success in the role. And you haven’t yet met that need.


So, 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? And here they are. Here are five easy but really powerful tips that will get you there.


Tip number one is don’t accept too short of 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 actually too short of 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 your role is one year. A year generally gives you a 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 when 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 of 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? Well, what I say is something like this, “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.” And I’ve never seen anyone have a problem with that response, so there’s no need for you to feel nervous about using it.


Let’s move on to tip number two. This one is talk about having a roadmap versus a plan. One of the problems with using the word plan, as in 90-day 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. And 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?


Well, the answer to that is to call your strategy a roadmap versus a plan. Let’s talk about why the concept of a roadmap works better. 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 into 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 naive 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 versus your plan and you can explain why the two are different. You’ll impress the questioner with your insight as to how the two are different.


Now, tip number three, start at the end, not the beginning. Starting at the end versus the beginning is a great approach not only for your answer but for your own planning for the role. And 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. So saying to yourself something like, “If I need to get from NYC to San Francisco in five days, I need to get to Las Vegas by day number four and Denver by day number three.”


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. And that’s because 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 than they would if you started with day one.


Now, day one 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 one, 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 nine. So that means by Month six, my team and I will have had to have gathered the preliminary analytics.” Et cetera, et cetera. And 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.


Now, here’s tip number four, 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 too. And 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 and take this in. 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, that leaders are supposed to make the complex simple. The reason that both these statements are so important is that 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 giving 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 one 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 the 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 she told the new organization that she expected it to last 3-4 months.


Phase two 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.


Was 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 six months.


Phase three 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 three 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 confused. However, the questioner was highly unlikely to forget the named phases, in other words, 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 number five, be sure to specify particular milestones where you will report back to your boss or key decision makers. So 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, right? The one who calls himself a change agent and then mows everyone else down? I know you wouldn’t be that person, but 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 important 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’s going to be important to ensure all your constituencies are aware of that and on the same page.


Just spell this all out in your answer about your first 90 days or first year, and your questioner will be impressed with how you’re already thinking about how best to communicate and keep aligned with the team.


Okay, there you have it, five 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.


All right, my friends. I hope this replay of our earlier episode sets you up well for the year ahead. And be sure to tune in for next week’s episode. If you’re a high achiever, a person who sets high goals for themselves and works hard to achieve them, I’ll be sharing two special tips that can smooth the road that you’re on.


High achievers like us don’t mind working hard, but that doesn’t mean that it should always feel hard. Wouldn’t it be great to start creating more of a sense of ease for yourself? These two tips that I’ll tell you about next week will help you experience that sense of ease more and more over time in your work life. In the meantime, however, I hope you have an awesome week ahead, and I’ll see you in our next episode.


Hey there, would you like some personal guidance about how to use the power skills of influence, persuasion, or presence in a particular situation in your workplace? Well, if so, we’ve got your back. Just send us a note explaining your situation to powerskills@significagroup.com. We’ll drop that email address in the show notes. We’ll feature your inquiry in an upcoming episode, keeping your identity anonymous, of course, and make sure you have some tips and strategies to help you navigate your particular situation skillfully.


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 www.significagroup.com.

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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. www.significagroup.com.