How to Plan in an Uncertain World

Episode Transcript

In this week's episode, I want to start with a paradox. Without a clearly articulated plan, interconnected and interdependent teams can't combine their efforts to reach a common goal. Yet in most organizations, planning is a political, performative time suck whose outputs are only loosely connected to the actual work that teams end up doing in the next three, six, or nine months.

We need plans, but the planning process turns out to be borderline useless. So what should we do? We have to rethink what we mean by planning. It has to become just as agile as the rest of our operating system. It cannot be stuck in our old ways of thinking and working. Why go through all the trouble of planning only to have a stakeholder ping you in the middle of quarterly planning to say, "It's not in the plan, but I'm still going to need your team to do this project for me in the next month"? I mean, come on — we can do better. It is time to do better.

Welcome to the Agile Marketing Edge, the first podcast dedicated to turning agile theory into real world marketing breakthroughs. I'm Andrea Fryrear, CEO of AgileSherpas and your guide on this climb to smarter, faster, outcome-driven marketing. Every week we unpack the what, who, and how behind agile marketing — from building high velocity workflows and slashing waste, to measuring what really matters and scaling success across teams. You'll hear quick hit strategies you can deploy today, plus candid stories from marketers who've traded chaos for clarity and never looked back. Hit follow wherever you listen, and let's carve the next switchback together.

Okay, it's pretty obvious this week that we are firmly in the planning part of the Agile operating system. So before we get into the nuts and bolts of what Agile planning is and how it works, we're going to need to pause for a moment and say something obvious: yes, you do have plans when you are Agile. I kind of can't believe that I am still saying this after almost a decade of teaching people how to be agile, but this is a common misconception that weirdly persists. Yes, agile teams have plans, we follow them, and then we plan some more. How would you know where you're going without a clear destination? Even if you're going to iterate en route, you still need to have a goal in mind.

We're going to talk about the difference between goals and objectives later in the episode, but you've still got to have an idea of where you're going even as you adjust the path you're taking to get there. So yes, planning is not antithetical to agile ways of working — let's just get that out of the way at the top. We need plans even in an agile environment.

In Agile Marketing in particular, if we don't have a plan of our own, we have no means of pushing back against any kind of outside last-minute interruptions or crazy ideas from other parts of the organization. If we don't have any plans of our own, why shouldn't we just accept any and all ideas from anybody and everybody around us? So I hope it's clear that yes, plans do matter — but the way that we arrive at them, create them, and then how we treat them and think about them after we've created them matters just as much.

Because if we think about what really old-school traditional plans look like, we can understand and remember why they just don't serve us in this new agile operating system. The way that we planned back when the world moved slowly and didn't change very much doesn't apply anymore. Back then we could create these really big, massive plans backed by months of market research and huge Gantt charts — with all of these "then this and then that" and "if this and then that" interdependencies — and all of those ifs and thens would actually happen. We didn't have to go back and reevaluate them very often because they actually played out in real life. It was only in moments of major crisis that we had to go back and readjust things. So the annual plan, based on a five, ten, or even twenty-year vision that didn't get adjusted very much, was pretty standard practice.

And now, if you proposed fixing your tactics for an entire calendar year and not adjusting at all for twelve months, you would probably get laughed out of a meeting. The world can flip on its head in a matter of hours now. Information is traveling so fast and trends are circling the globe in a matter of days. Entire new tools or social media platforms can roar onto the scene in less time than some companies could take to agree on the next quarter's budget. So yes — smaller plans that we're going to revisit a whole lot more often and with much more intentionality are going to be essential if we're going to have any shot at managing this new high level of volatility with any semblance of sanity, and with any shot at keeping people on target and managing their collective effort in the right direction.

But what exactly does any of that mean? A big question that leaders have to be prepared to ask themselves is: how much change are we actually comfortable accepting during the planning process, and in between deliberate moments of planning — these revisiting opportunities? How much adjusting is okay? And where are we set on not changing? Because some things should not evolve and adapt. That's not a question I can answer for you on this podcast, because I don't know your plans, your strategy, or your market. But you have to be able to sit down, have these conversations, and reflect in the midst of the planning process to decide where your level of flex is and what your non-negotiables are.

As you're doing that, I personally find it helpful to use a kind of 3D filter here — not like 3D modeling, but 3Ds like the letter. The three Ds I think are useful here are: define, discover, and deliver. You can think about this as a pyramid.

At the top of the pyramid, we have a clearly defined vision. We still need this — we still need to know the one-to-five-year horizon, and this is really focused on why we do what we do. In my opinion, this should be skewing more toward the short end of that time horizon right now, so maybe one or two years rather than five, because things are changing so quickly. But this isn't really going to change all that much. Why does the company exist? It's going to stay pretty clearly defined — it's the destination of the journey, or maybe your North Star. It's a vision statement. Most companies have this. And in our Agile planning processes, we're probably not touching this. It's not up for debate. This is one of those things that is not going to change in quarterly planning, especially in marketing, unless we're proposing some kind of major strategic shift. It's probably been handed down from the executive level, and we would have to make a massive business case for adjusting it in any meaningful way. So going into a planning situation, this is a given — something we probably won't concern ourselves with a lot, unless we need to go over it and make sure it is informing everything we're discussing during the planning process.

During planning, we're focusing most on the middle of our pyramid: what we are working on. This is where we're in our second D — discover mode. You want to chunk work out at this level into pretty big initiatives — think of these as OKR-level. We're going to go into a lot more detail about how to use OKRs, but these are usually pretty big and typically span about one quarter or three months, not multiple quarters or years. This is the discover layer: discover what's working, discover what the market wants, discover if there are gaps or new products we might want to develop, new campaigns, new channels. If you're in B2B marketing, your discover cycle is probably going to be longer, and so the things you are planning in this part of the process are probably going to be bigger, because your customers move slower and your buying cycles are longer. Adjusting what you're doing is going to be a slower thing, and you'll probably do this quarterly or maybe just a few times a year. If you're in B2C, you might discover new information more quickly, which means your planning cadence may need to be more rapid.

And then at the bottom of the pyramid — where the most stuff is, the most plentiful activities that teams and individuals are doing — we have the work that we deliver. This is the third D: delivering value to customers and internal stakeholders. Here we have tasks, projects, and small pieces of work with multiple steps and lots of detail. When we're in agile planning mode, we are generally not getting down into this nitty-gritty level, because we trust and empower teams to figure out the minutiae themselves after we have clearly defined that middle layer and articulated what is important and what needs to be discovered through the work being done.

This is really important because we are getting to the heart of why Agile planning is so distinct from traditional planning, and why we have to go through the rigmarole of planning activities in the first place. So even if you have PTSD from really bad planning — and we probably all do — you need to make this work. Because if you have a gap between vision and execution, you will have huge amounts of wasted effort. You still have a whole bunch of people who are going to show up and do forty hours of work every single week. If they don't have a plan to follow, all that time, effort, and energy is going to be pointed in a million different directions, because they do not know what is important. They might know why the organization exists, and they might know how to do their particular job, but they don't know what we're trying to discover or what we're trying to accomplish. And so they're just going to run around in a whole bunch of different directions and there will be no collective effort in any single direction — constant motion, but nothing actually getting accomplished.

This might sound scarily familiar to a lot of you, because what's going to happen is people will work out on their own how to fill their time if you don't give them guidance through robust and clearly documented planning processes about what is important. What we need to provide are agile, lightweight, adaptable plans that can point everybody in the right direction and allow their collective intelligence and experience to continually discover what is working, what's not working, and what to do next.

So maybe you have never experienced agile planning, or maybe you've only experienced the old distasteful kind. Let me give you a better sense of what agile planning is actually like. I'm going to borrow here from an HBR article on why planning doesn't have to be the enemy of agile. This is from back in 2018, but still super applicable to 2025 — we will link to the article in the show notes so you can check out the full context if you'd like. The four characteristics of Agile Planning articulated in that article are as follows. First, frameworks and tools are necessary to be able to deal with a future that is going to be different from the present in which we are planning. Second, we need the ability to cope with more frequent and dynamic changes — sound familiar? Third, we need quality time invested for a true strategic conversation, rather than planning simply being a numbers game. And fourth, we need resources and funds available in a flexible way so we can take advantage of emerging opportunities.

Let's go through these one by one, because I want to give you some tactical ways to actually achieve each of these in your next planning cycle.

First: frameworks and tools that can deal with a different future than the one you are planning in right now. Because that's like every day right now — we plan for one thing and then something crazy happens the very next day and we have to pivot. That's practically the word of the year. And of course, when we are using an Agile operating system or something akin to it, we have naturally built-in moments of reflection and adaptation. So make sure you're using them. Do not skip things like sprint reviews or retrospectives — they are there to help you. Don't let them fall off the calendar during the good, stable, non-stressful times, because then when you're trying to squeeze them back in during times of stress and change and flux, it's going to be nearly impossible to convince people to make space for them on their calendars when they weren't there during the good times.

Also make sure that you are bringing data into these moments of review and reflection. Don't just make them a verbal rundown based on people's memories of how things are going — you want to be able to look back at real, performance-based data. That can be things like campaign performance, whatever marketing KPIs you're tracking, or whatever performance metrics your teams are measured on. Look at those. Look at efficiency-based metrics. What's your agile team's velocity? If you track story points, what's your throughput — how many cards are you getting done in a certain amount of time? Do you have time-to-market data for your campaigns or projects? Whatever data you can get your hands on, if you have a project management system you should be able to pull some of this out of it. Look at the historical trends and see what they tell you. And if you can't get ahold of any of this, fix it now — get some kind of baseline as soon as possible, because the sooner you have a baseline, the sooner you can start to identify trends. If you don't have a baseline, that is your immediate homework. So: keep your retros, keep your reviews, incorporate data, and if you don't have a baseline, get one right now.

The second thing you need in your planning is the ability to cope with frequent, dynamic changes. And I can give you no better tool for this than the OKR — objectives and key results. Now, this term got really popular, got thrown around a lot, and therefore got misused a lot. So I'm going to give you the real way to use these, because if you use them the way they're intended, they are super powerful — lightweight, easy to understand, and easy to adjust on the fly if you need to, without losing their core goal or meaning. The objective can often stay the same in the face of change, even while the key results shift. So you can keep the essence of an OKR while adjusting based on what's going on with your team, the market, or your competitors. OKRs can be this nice combination of stability and flexibility.

Here's how that works. They have two parts: the O — the objective — and the KR — the key results. These are very different and you've got to set them up differently. The objective describes the overall thing you're trying to achieve, and this should be pretty significant. If we accomplish this thing, it is awesome and we're going to be really jazzed that we got there. We want it to be concrete — we will know for sure if we get it done, with no ifs, ands, or buts, and no debate about whether it happened. We want it to be action-oriented and a little bit inspirational — a bit of a stretch, maybe just beyond the threshold of what is definitely possible, but not too far. It needs to be realistic. When you talk to people about it, you don't want them rolling their eyes thinking "yeah, sure, okay" — you want people to actually feel like they could accomplish it. The objective can sometimes stretch over a couple of quarters — it might be a longer-term thing with the KRs shifting occasionally, and that's okay.

The KRs are more dynamic, which is what I was saying about that combination of stability and flexibility while your objective stays the same. The KRs are how we measure progress toward the objective. They are measurable milestones, and if we accomplished all of them, they would ladder up to achieve the objective. So they're not just a random hodgepodge of KPIs, to-dos, or tactics — they are all things that, if they happened, would get us to the objective. And whenever possible, they should describe outcomes, not just activities. We want them to be SMART — just like SMART goals, we want SMART KRs: specific, measurable, time-bound, reasonable — all of those things. So the KRs ladder up to your Os, and when the world changes around you, these are the things you can adjust. You probably still want to achieve your objective, but the way you're doing it might shift as the world shifts around you.

It's important to note that OKRs are not the same as goals. Generally speaking, goals tend to be more general, broad, and long-term — things like "increase our international customer base." That's a goal. An OKR, when written well, is specific, precise, and more medium to short-term — like "acquire 28% more customers from the UK, Australia, and Germany within the next three months." Under that objective we would have KRs: the activities we would be doing in order to accomplish it. OKRs are a great way to infuse your planning activities with that combination of flex and stability.

The third thing we need in Agile Planning is quality time for strategic conversation. And this is so difficult to achieve when everybody is so time-strapped and it's so hard to get time on people's calendars, much less convince them to do the requisite pre-work. But there's no getting around it — you have to have the right amount of time set aside where people are focused and present in the room and they have done the preparation. That's it. There's no magic trick here. You just have to do the work. You also need great facilitation in the room, whether that room is virtual or physical. You have to have good facilitation or everybody's multitasking, no one's paying attention, and you will not accomplish what you set out to do in the time allotted. No matter how big your team is or how long the time frame you're planning for, you should be able to get all of it done in two to three days every couple of months — if you have good facilitation and everyone did their homework.

And one more piece of this puzzle: once you're done and you've left the room, everybody has to abide by the plan that was set. There can't be any behind-the-scenes maneuvering of "can you just do me this one little favor?" Otherwise, the validity of the plan we all worked so hard on is undermined immediately, and everybody feels free to make their own choices about how they spend their time — meaning we wasted all the time planning because everybody's running around in a million different directions doing their own thing anyway, the same way they would have if we hadn't done any planning at all. So you have to hold the line. Everybody's going to think that they are the exception, that their request is the one thing that should be allowed to slip through the cracks. It is not. If one person makes it through, then everybody thinks they should as well. So: good facilitation, do the homework, and no one's the exception. Only then will planning actually support everyone's ability to focus, push in the same direction, and accomplish the objectives you've worked so hard to set.

Last one: the fourth component of good agile planning. Funds have to be available for emerging opportunities. Said another way, the money has to move with priorities. This is why lean agile procurement is an emerging discipline. If we set the budget in January and then meet three more times a year to re-plan but the budget doesn't change, what's the point? So it's time to get creative here. Could we fund priorities instead of projects? Could we fund outcomes instead of activities? We've got to change how we're thinking about this part as well.

I am not a Lean Agile procurement expert and I'm not going to pretend to be — maybe we'll have one on the show in the future so we can dive deeper into this topic, and we'll link to some resources in the show notes if this is a pain point for you. But your money has to match the way that you're planning. Otherwise, why go to the trouble?

And I want to wrap up with what may be the greatest quote ever to grace the pages of the Harvard Business Review, from the same article I quoted earlier about how agile and planning can in fact go together: "Universally valuable, but desperately unfashionable, planning waits like a spinster in a Jane Austen novel for someone to recognize her worth." So be the wise suitor who sees the value of agile planning — because the world will never be moving too fast for it to be valuable. No matter how unfashionable it may become, it is our best and only way to keep from wasting time and energy on disparate, misaligned efforts.

If you're wondering if planning is your biggest problem or if you should be focusing your attention elsewhere in your operations, you should check out our free Marketing Agility Assessment. It helps you discover how your team stacks up on speed, focus, and effectiveness by giving you a score across nine dimensions of how you get marketing work done. It takes just ten minutes and you'll get a clear picture of your team's overall operational health. We'll put the link in the show notes, and you can always find it at AgileSherpas.com. Till next time, I'm your host Andrea Fryrear. Don't forget — the struggle is real, but so is agile marketing.