The Ambition-Confidence matrix
Stakeholders are dreamers. They see the current situation and dream up a better future. When we talk about strategic roadmaps, this is exactly what they have in mind: steps to take us from flawed point A to improved position B.
Their software teams have a more analytical mindset. They hear "position B", look at the current situation, and envision all the challenges on the road.
That's not a character trait, per se. Engineers are often wild dreamers in their own side projects. But when you get paid to take it from point A to point B, you mainly see the practical challenges.
Stakeholders see opportunities; engineers see problems.
This is reflected in the kinds of plans I see out there. When stakeholders make a slideshow of the plans for 2024, it's always overly ambitious. They'll launch a new app, improve the performance, get hold of the German market and rewrite the UI of their existing platform— all with the same team. Stakeholder-driven roadmaps are ambitious but unrealistic.
When engineering teams make the plan, they tend not to make one at all. They can tell you what they're currently working on and will show you a backlog of things they just as well might build if they ever have the time. Team-driven plans are realistic but never ambitious.
That makes sense. If you see the world in opportunities, you'll plan to capture as many of those as possible. If you see mainly problems, you want to keep your options open and not paint yourself into a corner by making promises.
A good roadmap is a balance between ambition and confidence. It's a trade-off. Quelle surprise.
Let's take a look at this matrix and its outliers:
Engineering paradise (Low ambition, high confidence)
In this situation, the balance is shifted in favor of playing it safe. There are little to no long-term plans and promises. Teams focus on what they are currently building. It's a dream scenario for just-let-me-code developers, as there are no deadlines, no plans, and no responsibilities other than programming.
A team that refuses to plan, creates an engineering paradise to avoid these kinds of responsibilities. They'll hide behind their manager while making sure that manager doesn't have the tools to do their job.
This results in unhappy stakeholders, as Engineering is seen as a stagnant black box that burns money but doesn't deliver tangible results. Their output is predictably low.
While this might sound like a caricature, it's a common reality. There's an entire startup ecosystem of small SaaS companies that sell shadow IT solutions to stakeholders who feel like their own teams can't be trusted. It's a real and expensive problem.
High-performing team (high ambition, high confidence)
This is the dream scenario every "Agile coach" and startup guru will try to sell. The stakeholders have sky-high moonshot ambitions, and their teams can rise to every challenge. It's a healthy balance for those world-class organizations that can pull it off.
Experiment culture (low ambitions, low confidence)
Some teams are in such an uncertain situation that planning becomes futile. A typical example is the pre-market-fit startup. If you have yet to learn your customers and you still have to figure out what you're trying to build, there's no use in long-term planning.
In this situation, stakeholders understand that the team is still figuring out the market. The team is capturing feedback by building MVPs and running experiments. There's the mandate to try small things and see what works. The ambitions are low, and so is the confidence. That's also a healthy balance.
PowerPoint fantasy (high ambition, low confidence)
Finally, there's the stereotype we all know. It's the stakeholder who creates a strategic vision roadmap for the coming year that's full of features, aspirations, and buzzwords. These roadmaps are presented to the board and feel like a job well done. Everyone leaves that meeting with a good feeling.
Unfortunately, PowerPoint is far removed from the actual work floor, and these kinds of roadmaps are already behind schedule while we're still adding slide transition animations.
In such an unbalanced situation, stakeholders promise the moon and hope their teams can fly.
Those are the extreme scenarios, but each team is situated somewhere on the matrix. It doesn't matter whether you live in chaos or the ambitions are sky-high. What matters is that you try to find the right balance. You want your stakeholder's ambition to match the team's confidence. You also want to avoid the blue quadrants. Even if stakeholders are happy with low ambitions and high predictability, the team can handle more.
Ideally, you want to be somewhere on the dotted line between an experiment culture and a high-performing team. That's the healthy balance between dreaming and doing.