Free Tools: The 90-Day Tool Every Leadership Team Needs

Too many priorities. Constant firefighting. Feeling like you made progress in 25 different directions but did not actually move the business forward. Sound familiar?

In this episode of Sessions with System & Soul, Benj Miller and McKenzie Decker share a simple but powerful tool for setting quarterly objectives and actually hitting them.

You will learn how to:

• Identify the bets worth placing for the next 90 days
• Cut your “must-do” list down to the most strategic moves
• Create alignment and clarity across your leadership team
• Avoid the trap of working in the business instead of on it

Whether you lead a senior leadership team or manage a department, this framework will help you focus resources, accelerate progress, and turn strategic plans into real results.

Start applying these ideas in your next leadership meeting and see what happens.

Sessions is hosted by Benj Miller and McKenzie Decker

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Chapters

• 0:00 The challenge of too many priorities
• 3:48 Why 90 days is the sweet spot for focus
• 7:21 Choosing the right bets for your quarter
• 10:44 Cutting your “must-do” list down to size
• 14:30 Getting the whole team aligned on priorities
• 17:56 Turning strategy into weekly action
• 21:41 Avoiding the trap of working only in the business
• 25:54 How to handle shifting priorities mid-quarter
• 29:38 Celebrating wins and learning from misses
• 33:16 Final thoughts on leading with clarity and focus

Transcript

Benj: 0:36

Hey, welcome everybody. You're here Sessions with System and Soul, with myself, Benj Miller, and my partner in crime, Mackenzie Decker. And, we're gonna have some fun today, mainly because we're gonna be talking about something that frustrates a lot of organizations and a lot of organizations really, they get stuck, they get frustrated, they seem like they're dealing with the same thing over and over again. And so this is a free tool episode. And so today we're gonna talk about one of the tools that we. Consistently use to mature the organization. Get out of some of that frustration and Mackenzie's gonna lead the way. So you ready? Mackenzie?

McKenzie: 1:13

I'm more than ready.

Benj: 1:15

More than ready. Let's go.

McKenzie: 1:17

In previous episodes, we've talked about having a weekly meeting. And some of those, basic practices are the things that can be the most frustrating and I think the most impactful. I think, any organization I've been a part of, and I know for all of our clients that we work with, there's just this constant, there's a constant need for priorities, right? every organization needs priorities, but that seems to be one of the hardest things to decide to stick to, to focus on for any team of any size. That I've ever seen. So it's a super common problem, and I think what happens, and I hope, I'm sure that whoever's listening to this, if you're joining us today, you can relate where you've been in a season where there's 25 things you could do or that you're trying to do, and then you get to, the end of the year, you get to the end of the quarter, whatever timeline you measure. Progress on and you're like, wait, what did we get done? what were we just re were we reacting to the things that fell in our lap? Or we made incremental progress in 25 categories. And at the end of all that, it can feel defeating. when it comes to did we work? On the business? Did we progress as a business or did we just get a bunch of stuff done? So the tool we have for this is, again, we're gonna, we're gonna be able to talk about it in just a few minutes here, and it's gonna sound really simple, but I would say it is not easy. And we can talk more about that and why it's not easy, and how to navigate the roadblocks that come up as we go. But the tool is what we call objectives. More specifically quarterly objectives. So quarterly objectives are the 90 day goals we set as an organization to help us get the right things done and work on the business. I'm sure everybody here has heard that phrase before. the, phrase on the business means that we're working on things that help us grow, scale, mature. It's the things that you. As a leader, you have like in the back of your mind like, man, we've really got to up level X, Y, and Z. But those things stay on some list somewhere and they never get done. And then we're just, again, we're reacting we're dealing with the problems of today or the problems of the quarter. And we don't get those things done. So what we wanna do is actively prioritize the working on the business stuff so that we make real progress year over year, quarter over quarter. So that's what's an objective is. Can you, you see this play out all the time. One of the things our binge and all of our coaches do is help teams set these. Every 90 days. So Ben shows up in the room and he's like, all right, how'd we do? And then what's coming? So can you describe, just as you've been in the room, what does that conversation look like and what do you see? As people try to even land on the right things.

Benj: 4:13

Yeah, we talk a lot about making bets because like you said, that stuff goes on a list and just never gets activated. The other thing that happens is you put everything on the list or you change the list so often that you are not making progress on the things that you said. Were on the list, and so when we sit down to do this. First thing we do is we really try and work on the business. So we've gotta get everybody in the room out of the minds of I am in this function of the business, and look holistically at the business. And then really try and get it down to as few objectives as we possibly can. The most important objectives. And so this is the thinking in bets. What is the thing if we're gonna take our resources, time, energy, money, focus people, and we're gonna put those chips on the table. Then we need to mo put it in the most strategic place because there's an opportunity cost. If we put it on red, we can't put it on black. we're making that bet. and the reward better be worth the risk if this is going to be one of the most strategic bets we make. As an organization in the next 90 days, or some of these objectives are actually eating away at our priorities for the year. So we've got these big priorities for the year. We've got four quarters to break those down and make progress toward the, so either way you're looking at it, we're really thinking about what is the most strategic bets that we can make. herb Keller, who's the CEO of Southwest Airlines, is famous for saying we have a strategic plan. It's called Doing Things. Which is awesome and I love it because it un mystifies strategy, but there's strategy and what are the things that we're choosing to do as a team, and then how are we gonna actually get this done?

McKenzie: 5:57

You're, yeah, totally. And it's, like I said, it's simply said, but it is a challenge to get to that level of clarity. When you're in that room, what do you see as the tension oftentimes? In those teams is they're trying to decide what to work on.

Benj: 6:11

One of the tensions is, things that are in the business. the CFO has an audit that they have to do, but they have to do it every year. Yeah. The sales guy has a sales quota, but they've got that every quarter. So there's the tension of, the working in the business, taking away from working on the business. There's the tension of too many priorities. There's the tension of, anything that feels administrative. Is probably not a strategic bet. and some of that stuff has to get done there. It's really funny to just ask the question sometimes. what if we didn't do this? You are like, ugh. But we, it's in that should category, like we should do this. Okay, but what if we don't? What if we just don't? What if we do it next quarter? What if we do it next year? What if we, delegate it? What if we outsource it? What if we, how do we. Focus, the energy in the room, the energy in the organization toward the most important thing.

McKenzie: 7:07

Yeah, we've experienced that. I, would, say we, the, challenge that you're describing is. It's my job and I've gotta do it. And then there's also we've gotta make time and create space for the things that are even outside of the to-do list. So yeah, there's this tension there that has to be managed. But,

Benj: 7:28

there's also a, like I'm the worst at this. A tension toward recency bias of oh, last night on Instagram I saw this new thing and it's now the most important thing that we should do in the organization and Right. I'm so guilty of that. And like the problem with that is it might be right, but next week there's gonna be another one of those, right? So even having the list of potential things that could be objectives is super freeing for me because this idea, whether it's great or not, has a place to go and simmer all the immediate excitement down. And then if it's there, come quarterly time, great. Let's decide if it's one of the most important things. If it, more than half the time you look at that list and go, what was I thinking? like, why no, we're not doing that.

McKenzie: 8:17

Yeah. Let me break this down for them in case this is a new concept. But so they, the way that this works, so objectives are determined every 90 days, but what Ben is describing is. Over that 90 days, there's a growing list we're creating. We've got a parking lot for big ideas, for things our big shoulds. The things that we know we want to do to help us move towards our one year or three year goals. So we're literally building maybe even the list behind you is a, on your whiteboard is our opportunities list,

Benj: 8:50

little bit

McKenzie: 8:51

Our future objectives list, but we wanna create, over that 90 days, we create this parking lot list so we don't get distracted from the things that are already decided that we're already working on. And I know that's extremely difficult. For, the visionary types. just as for me, it's, hard to. On the other side of that, move past some of the things that we just need to do, to make progress in the day-to-day of the business. So we've got, I've generally got the 5,000, 10,000 foot view and you're over here in the 30,000 foot view. And we're trying to find somewhere in the middle that our objectives can land. But we wanna create that list over a 90 day period while we're working on our objectives. And then we get to this date on the calendar that we plan and we put. I think right now we're putting like six hours for this day where we come together as a leadership team. So anyone who is a, leading a department or that you would say they're like, your generals or your executive team are gonna come together for that six hours. And they're gonna spend a portion of that time reviewing how did we do in the last 90 days? And then they're going to spend time taking that list out, looking at the parking lot, and then deciding these are the things that we need to examine for potential objectives in the next quarter. We've got this list and then we do this thing called . Usually there's I don't know what, 10 to 25 things on that list. And everybody, has the ability to put something on there. So there's gonna be things related to certain departments. There's gonna be things related to certain functions of the business. And so we can't do 25. you could try, but what we're not gonna get very far. and so what we do, we have this little, process we call keep kill combine. And so you basically just take that list. And have a conversation around what are the most important things, what can wait, what should we not do? It's such a good question. And, then we're gonna get down to just a handful of things that we can actually do in the next 90 days. So it's gotta be super realistic. Generally we don't want more than, if you've got like a team of five people, you don't really need more than five objectives. We wanna keep it to one per person, because. Otherwise, we're gonna overextend ourselves. We're gonna lose that focus. Yeah. So there's a, and this may sound a little bit like, I don't know, intimidating in some ways, because if you got 25 and you only do five, what happens to the other 20?

Benj: 11:25

And sometimes they turn into phantom. I've gotta do that anyway. And it's okay, maybe. But the important thing is we're saying as a team, these other three, five, whatever are the most important. Another way that I've been doing it a lot, if you've got a lot on that list to narrow it down, it's just to give everybody in the room three little dots. Sticky dots. Yeah. And so they're literally voting like, Hey, if we only have three things. And if somebody really wants to put all three dots on the same thing, they can. But they're, basically placing their bets on the bets, and then we use that to whittle it down. That's been really helpful. yeah, I, totally, I wanna reiterate the like less is more. Absolutely no more than the number of people in the team. It doesn't mean everybody, everybody needs one. some of the best quarters I've seen is when there's six people in the room and you have three and everybody's pitching in and working together. it doesn't always work, but sometimes ask the question, is there a theme for this quarter? yes, this quarter, we've gotta like absolutely improve our internal operations. Okay, let's dial that in. Let's point everything toward that. theming is another way that you get everybody cross-departmental aligned toward a common thing, and then they've all got their little aspect of how they're gonna move the needle.

McKenzie: 12:46

Yeah, I like that you, you said a align, it aligns the team.'cause I think that's one of the most beneficial things about making these decisions in these quarterly. Objectives is it really helps us decide together what's important because like you said, the recency bias or the shiny object or the fire that happens, in the business three months later or two months later, can become a distraction. And it gives everybody, it gives everybody the ability and the awareness to say, that's not what we decided that we were working on. Yeah. This is what we already decided. so that can, wait. so that alignment and that. That kind of clarity is a huge part of this. So we can't just, one thing I, wanna clarify what, we can't just whittle it down, decide we're gonna do X, Y, and Z. We've got a list of three to five things. That's, part one. The other thing that we wanna do is get it really clear and defining, defining what we are trying to do. What we are trying to do, what outcome we're looking for, and how we're gonna know when we've done it. Yeah. How do we know that we hit a hundred percent? Because that's the other frustration I think that we all feel is we could say that we're gonna do these three things, but what does that really mean? And we may all have a different idea of what done looks like. And so we can't, commit this kind of time and energy. To that unknown. And so we're gonna get really clear on how we define these things as well. So I'm gonna walk it through really quick.

Benj: 14:17

first, I love that you're doing this 'cause you're so good. You're so good at all of this. really dialing in the details and making sure everything's clear. One disclaimer, if. We're really talking about stage two, stage three, stage four organizations. If you're a stage one, like you consider yourself like in that startup mode, still trying to figure out, your product market fit your go-to-market strategy, sometimes 90 days is just too long.

McKenzie: 14:42

Yeah.

Benj: 14:42

So I, would recommend pulling that down and doing some 30 day or 45 day objectives. And obviously they're, not as big. They've gotta have a smaller scope or part of a bigger scope. But what that allows you to do is go in faster cycles where you can reprioritize more often.

McKenzie: 15:04

Yeah, that's a good point. We've even had, you have a period of time where you've got, maybe there I would, crisis is seems like a big word, but if you've got like a. If there's something external that's happening in the business that's causing you to have to be a little bit more reactive. Like I know that when, as we went through the pandemic a few years ago that yeah, we moved all teams moved to 30 day objectives.'cause there's a lot of unknown. And so that can still be true for any business, whether it's some kind of outside circumstance or it's just. The stage that you're in.

Benj: 15:35

Yeah.

McKenzie: 15:36

The clarity of defining them though, whether it's 30 days, 45 days, 90 days, whatever it is, so important. And so there's a couple things that we wanna lean into as we define objectives. First is we wanna have a really clear mission for that objective. Meaning like we wanna have a. A clear, compelling statement that tells us what outcome we're looking for. And the reason we wanna do that is because there we may make, we, can decide that there's something important that we need to work on. And over time we could create the world's most perfect plan around it. But over time, we're gonna learn, we're gonna learn more information, we're gonna encounter roadblocks, we're going to, things that we thought would happen are gonna fall through. And if we just define it by this perfect plan, we're gonna get to a point where that objective is muddy. It doesn't make sense. We've totally lost the plot on it. And yeah, we need to define the mission in such a way that we're able to say that's the hill, that's the flag that we're headed towards. We're gonna get there. However we need to get there. even if the route that we plan to begin with is not available to us three weeks in. We wanna be clear about the outcome and what we're looking for when it comes to defining an objective.

Benj: 16:57

Yeah, this is so good because one of the things that we've experienced and I've seen my clients experience is, having, when you do define it, having it an outcome that you don't actually control. So this happens a lot when you're trying to do something with a strategic partner or, an m merger and acquisition or anything. that there's even, buying a property or something, a new office or a lease or something, there's so many variables outside of your control and you get to the end and you're like frustrated. I did everything I possibly could, but they, but, the other side of the transaction weren't ready to move as fast as we wanted to move or ran into this, audit, whatever it is. Like you run into stuff and that can be very demoralizing because you're doing every, all the effort. But you're not reaching the goal. So when you're sizing these up, trying and, defining them, making sure that you define those ones, defining the contingencies, they can mess it up. But also what can we, frame success based on what we put into it and see what the outcome. Is from there.

McKenzie: 18:09

Yeah. It's such a good point to say like it really should be thinking in terms of what you can control.

Benj: 18:14

You already said it better than I did, so

McKenzie: 18:18

I, the, it's really good what you're saying about having it be things that you can keep within your own control, because like you said, there's gonna be all kinds about. External circumstances that make it, it could take it off course. So one additional thing. So we're gonna start with a mission. We're gonna state that really clearly the outcome we're looking for, the outcome that we can control. And then we are also gonna name what we call key results. Key results are. Essentially it's like a high level project plan of if it's a checklist and we could day one start here and day 90 in here, what would that list be comprised of? And so for someone like me, this is my favorite thing everyone says, I'm like, okay, we're not just let me say this too, before I. I like, I need to back up. We're choosing things that take 90 days at least, or 30 days or 60 days, like we're choosing something that's pretty hefty. As far as like it, it's got multiple steps. It's gonna involve multiple people. It's gonna, it's going to take resources like we said. So we can't just get, we can't just say in a sentence, this is what we're gonna do and then hope that it happens in 90 days. So we want, we wanna plot out like over a timeline, what would be step one, step two, step three, so that we really know we're headed in the right direction and we're able to say we're making progress towards it.'cause I know we've all had an objective or a project that we've been a part of where it's like. Yeah, we're gonna go do that. And the meeting had all this energy and we're like, we felt really clear in the moment. And then we get a week away and we, we had a long weekend or something. You come back on Monday, we're like, when in the world did we just decide? I don't even know what that meant. So we wanna get,

Benj: 19:59

when am I gonna do this?. Like I signed up for all this and now I'm back at my desk and I have all these direct reports and all these emails and all these meetings. I have no idea how this is even possible.

McKenzie: 20:11

Exactly. And I, so the key results are really gonna help us decide what are the key steps, the key outcomes, the things that we're gonna do to get this done. One thing that, that I've noticed too is as I lead our team and we, decide our objectives and then, a week later I go in, I go and. And invite them into the conversation. So I'm explaining what we've decided and the key results are a great place for me to show them where they're gonna be playing a part in it. And I can say, you're gonna be owning this step when we get here. this is all you. Let's clarify what that means now before we get there. Key results are a good way to define what we're gonna be accomplishing in the objective over time. And then we're also gonna set milestones. And milestones are essentially, you can pull from your key results for this, but it can be a, it needs to be something that we can look at in 30 days or 60 days and say, Hey, is this done? Are we making progress? And again, this is like a benchmark so that we don't get three months down the road. And we're like, what in the world did we just like? We didn't get anything done or what did we decide? I can't remember what we were looking for. So we wanna give that moment of what we call show and tell to really it. It's a, it's like an accountability thing, but it's also another way to look at it is that show and tell gives the team the opportunity to speak into something before it's done to help you pivot or. Adjust or get feedback as you go. we set those milestones at the 30 day mark. So a month in, and then two months in, at 60 days, and literally do a show and tell for our objectives. The last thing we wanna do is we just wanna, two things we wanna do. We wanna set a clear owner and we wanna set a due date. So you really wanna lock in when are we, gonna say this is done? And then who's gonna own it? And owning it means that person is really responsible for doing all that definition that we just talked about and carrying the ball. But they are, they're really there to almost like project manage. Their objective and they can invite in whoever they need to. They can ask for support. They can delegate pieces of that, but they're really the one at the end of the day who has to report on is this done or not done and what outcomes did we get to?

Benj: 22:35

Yeah, you're avoiding the word, but they're accountable for it.

McKenzie: 22:40

and I think I hesitate 'cause it can be such a negative, it has such a negative connotation in some ways. but yeah, accountability in the right way can be really powerful. This is also this clarity and this kind of, focus and you said it earlier, this kind of alignment of a team can be so dignifying, it feels. Amazing for a team when they have this kind of, they're, they've got three things in 90 days that they're gonna really drive towards on top of all their other work. But they're gonna drive towards this together. They're gonna do this work together, report on it, talk about it over that 90 days, and then we get to go, did we do it? Yes. We got a hundred percent of it done. that's a huge win. It's. Yeah, it's a, it's that kind of like rising tide lifts all ships momentum that happens when we're able to create this kind of progress over time, rather than running at so many things at once.

Benj: 23:39

Yeah. a couple of notes on that. Is that like winning creates momentum. And so if you've never done this, you have a huge backlog of potential objectives, and you're gonna want to go like hardcore, but really getting a rhythm of winning with these quarterly objectives Over time. over time, you'll be able to increase, maybe the quantity, but also the scope of them because you're. better equipped to get lots of people in the organization involved. And so just, I'm just recommending that you start, small, and then feeling that momentum. That's why we check in on these in the weekly sync every week. Is because we want if, we set it and don't come back 90 days from now, even if we did get them all done, which would be a moment to celebrate, we missed the opportunity to celebrate it along the way. Hey, we're crushing this. We're doing this. Hey, we're probably like two weeks behind on this. We're gonna need some help. I'm stuck on this. I need your help. It's more of a team sport when we do it together like that. And winning's always more fun when you're playing as a team and really operating at that level. There's one other question I love to ask in the session room as people finish defining their objectives. and, a lot of times the answer to this question is just no, there's nothing. But sometimes it unlocks magic in the room and the question's, this what, is there anything that we could do. Or decide today that would greatly accelerate the success of this objective. So I'll give you an example of what that is. Is there anything we could decide today that would greatly accelerate the success of this objective? We were in a conversation. We'd already defined this whole objective. It was around implementing a CRM. There's always some CRM blah blah, blah in companies. But, it was a big switch to a new CRM. So by the end of the quarter, I forget how far they wanted to get on this thing, but the first 30 day milestone was making a decision. On which one they were gonna go with. They had already done some preliminary work and they just needed to make a decision. And somebody in the room meekly raises their hand and say, can we just go with blah, blah, blah, whichever one that was their front leader. And everybody around the table was like, yeah, just do it. Boom. We had magically done 30 days of work with one quick conversation. the other thing it can do is surface. Any underlying like concerns or ideas that people have regarding that objective and again, accelerate the potential success of it. So that's a great question as you're wrapping up this exercise.

McKenzie: 26:14

Yeah, that's strong. So just to recap and then we got a resource for you that's gonna help you do this. We, when we set objectives are gonna be 90 day goals generally. But if you've got, a smaller business or, you're just trying this out for the first time, try it for 30 days. Try it for 60 days. so we wanna set a mission, a clear statement of what outcome we're looking for. We wanna define key results, the project plan, the checklist of what's gonna get done. as we go along, we're gonna set milestones so that we're actually showing and telling the work as we go. Set a clear owner, a clear due date. We're gonna ask at the end of that. Are there any decisions we can make that would accelerate this? And again, we wanna make sure that these are things that help us work on the business and not in it. So if the CRM needs to be on the list, great, but if the CRM is just somebody's job, it's somebody's job. that, that's the recap of objectives, quarterly objectives. I hope you give it a try. You can do this at a senior leadership team level. You can also do it at a departmental level. If you're not leading an organization, you're leading a team. Absolutely. So give it absolutely. One of the, we have a tool for you to try out here. we've got a downloadable guide that's five conversations that leadership teams should be having, but oftentimes aren't. And this is one of them. We call it the focus conversation. in that guide, there's all kinds of questions for self-reflection to discuss this with your team. And build your list together and get that initial list going, and then some questions to jog your thinking and maybe look at the business in some new ways. So this entire, step-by-step plan is in that guide as well as these kind of thought provoking questions on how you can do this for yourself. the, that link will be in the show notes. You can download that for free and give it a try.

Benj: 28:10

Sweet. I'm remembering how much work I have to do on my quarterly objectives, so I'm gonna get outta here. Hey, if you are enjoying the show, then share it with somebody else. Share it with somebody on your team. Maybe you can rally some, a meeting to get some quarterly objectives and make the next 90 days the best 90 days you've had in your organization. special shout out to fist Bumps who helps produce this show. Great partner of ours. Really appreciate all of their support and guidance. And we will see you next week for your next session.