Managing Expectations Around Roadmapping

You probably came to this series just hoping to create a simple roadmap. Well, you’re going to do that. And, if this is your company’s first time going through an actual process to create a roadmap, then, in the process of creating that roadmap, you’re going to end up doing so, so much more. All of it will be good. And some of it, additionally, will be painful.

Why will some of it be painful? Well, when you think about it, in order to have any hope of creating a realistic roadmap, your company, and the teams within it, have to have all these things nailed, as a prerequisite:

A business strategy that’s a north star for your product strategy
A product strategy that helps inform hard decisions around priority
A realistic picture of the resources (i.e. people) who are your total capacity
A realistic picture of how much work your resources can accomplish in how much time
A realistic accounting of all the non-roadmap stuff your resources have to do just to keep the business alive
A commitment to various project’s requirements that stays still long enough to estimate their basic size
A realistic picture of how much time those requirements will take to implement with the resources you have
Some mapping of projects to business value in order to know which projects make the cut and which don’t
A clear decision making structure so you know who can and who cannot choose winners and losers
A clear roles and responsibilities structure so you know who decides requirements and who doesn’t
A basic acceptance of the simple fact that it’s not possible to do everything, everywhere, all at once

In my own practical experience, if a company doesn’t have a clear roadmapping process, it very, very likely doesn’t have one or more of the elements in the above list, either. And, attempting to create a defensible, predictable roadmap will absolutely expose those deficiencies. Or, you will fail to create a defensible, predictable roadmap. It’s either-or. Hopfullly, when laid out starkly like that, it’s logically clear why. But, you’d be surprised how many companies have limped along without acknowledging that reality.

Once you start roadmapping in a real, structured way, the organization won’t be able to ignore these dysfunctions any longer. They will be brought into painful, highened clarity. But this is all a good thing! Not seeing these issues doesn’t make them go away, it just makes it impossible to address them. So let’s surface thems so we can get down to the business of solving them!

Expectation #1: this will generate a little conflict.

Roadmapping is a zero-sum game. The organization only has so many resources and it usually has more ambition than it has ability to fulfill it. Resolving this will necessarily create conflict.

In fact, in my own personal experience, if your company hasn’t managed to create a real roadmap yet, it’s probably becuase it’s been avoiding this conflict. And if you don’t experience conflict while creating that roadmap, you’re probably skirting the hard questions that need addressing. If all this were easy, someone else would have done it already and you’d have no business opportunity at all.

Expectation #2: this will surface uncomfortable truths outside the roadmap

This process tends to shine a spotlight on several kinds of previously-hidden or unacknowledged organizational dysfunction, whenever it exists. Some uncomfortable, previously-anacknowledged truths I’ve seen surface as a result of rolling out this process:

The business doesn’t actually have a strategy and has just been winging it
Roles and responsibilities are fuzzy and nobody knows who is empowered to do what
The people we’re trying to hold responsible for doing things aren’t truly empowered to do them
One or more otherwise-powerful people don’t/shouldn’t have a say in everything they think they should
The organization doesn’t have the capacity to do what it needs to do to succeed
The organization is totally unfocused and doing too many things at the same time
Priorities have been historically set by force of personality of a few individuals instead of rational business criteria

None of these truths have to do with the roadmap, per se. But, every last one of them becomes glaringly obvious when you do try to create a roadmap. The best you can do is make the truths visible, let them speak for themselves, highlight their connection to hindering the building of a good roadmap, and continue to soldier on as best you can.

Expectation #3: you will discover that some good things will never get done

Until forced to see otherwise, most organizations persist in the collective fantasy that they can get everything they need to get done, done, and the only thing that’s stopping them from doing so is figuring out how to make people work faster or better. Usually, they’re wrong. Almost without exeception, most organizations want to do more than they have capacity to do, everywhere, all the time.

After all, which organization would you rather lead: one that’s always pushing the boundaries on achieving more, or one that carefully and conservatively picks its way through a bland landscape of low expectations? When put that way, it’s clear that having more ambition than resource is a good thing! Well, it’s a good thing…up to a point.

After a certain point, say 110% of capacity, this excess ambition actually slows the organization down. It leads to getting less done. People start tripping over each other, burning out, making mistakes, cutting corners, etc. And nobody wants that. So, it’s important to have a sober and accurate picture of ambition vs resource, so leadership can make informed and ambitious calls on pushing the right amount in the right direction for the right cost.

This process almost always shows, quite definitively, that this fantasy is false. This sucks. It’s disheartening. But, actually, you are doing the organization a favor. Reality dictates that that stuff already wasn’t going to get done, it’s just that the organization didn’t know it yet. Now, you’re doing the organization a favor. You’re giving it the visibility it needs to define and correct its priorities, earlier, in a way that increases its chances of success. This is a good thing!

Most importantly, don’t panic. Try to help other people not panic, too. Relatedly…

Expectation #4: people might become afraid to ask for anything

This surprised me, but I’ve seen it happen more than once. The organization suddenly flips from “I’m asking for everything I want as soon as I want it and will get mad if it’s not delivered immediately” to “I’m scared to ask for anything from the engineering team unless its absolutely critical because they are too over-committed” This is a worse problem than it seems. This can lead to your entire organization freezing up in fear. Seriously. It’s an existential threat. You’ll suddenly find the organiztion letting problems fester for way too long. It adds barnacles to the hull of your business. If you don’t overcome it, you and everyone around you will fail.

Once you have noticed this happening, you now need to aggressively switch into a mode of proactively soliciting and encouraging ideas from the business. Be very encouraging. Be optimistic. Be positive. This will be very difficult because you will still be emotionally scared from the previous state of things, when everyone was demanding everything all at once. Do your best, anyway. If it helps, you can generate some emotional empathy in yourself by reminding yourself that these people are seeing, finally, the same horrifying zero-sum reality that you’ve been living for probably your whole career. It was uncomfortable for you, right? Well, it’s just as uncomfortable for them, and it just slapped them across their face as a surprise, probably for the first time ever. Give them a moment to recover.

Expectation #5: you need to be a Director or above to make this work

If you don’t have a first-hand, personal relationship with the “deciders” of your organization, and you try to roll out this process, then you will very likely fail. Likewise, if you only control, say, 1/3 or less of the “resources” being managed in this process, then you will likely fail. You don’t have to be the actual CTO. But you need to at least report to them. And you need to have sufficient influence over and trust from your peers. Are any of those things not true? Then focus on changing those things, first.

Expectation #6: it will take several planning cycles to get right

The first time you do this will be laborious and messy. The second time will be less so. Perhaps, if you’re lucky, the third time will start feeling comfortable. The fourth time, ideally, starts to feel like a real groove. By the third or forth time, ideally, you’re not starting from scratch every quarter. You should have a tidy backlog of well-defined, well-estimated stuff that almost, but not quite made the cut. The first time you’re doing it, though? Well, you’re starting from zero. And you’re having to get everyone on the same page about how the process, itself, even works. And you’re dealing with all the non-roadmap truths that the new process surfaced for the first time. It’s hard. It’s a lot. Tough it out, anyway. The subsequent times will be easier.