Have your stakeholders estimate with you
What would you do differently if you had the superpower to flip this conversation around?
As a software leader you often end up navigating the uncertainties of your stakeholders. Having them collaborate in the estimation process can make a significant difference in achieving successful outcomes. Let's dive into the following key topics to enhance collaboration and streamline the process.
Today’s Crafting Tech Teams issue is all about the conversation surrounding estimations, forecasts and roadmaps. You will learn the following:
Human nature behind certainty and planning. The natural, human inclination is to seek certainty by planning. The negotiations happen around areas of risk and discomfort for each individual human. That is what influences forecasts, not the numbers.
How can you be sure the estimates are knowable? Sometimes you don’t know and your stakeholders don’t believe you—or want the certainty that you do know and find out. The magician archetype is strong with engineers. When backed into a corner, engineers tend to lie to stop the pressure. Most estimates are forced onto paper like this.
Stakeholders have constraints prior to asking for estimates. Understanding the constraints faced by stakeholders before seeking estimates is essential. Move the conversation towards their constraints, rather than asking to change them.
Conversation patterns that annoy vs. foster collaboration. Effective communication is crucial during estimation discussions. We'll examine conversation patterns that hinder collaboration and strategies to promote a healthy exchange of ideas.
Estimation gives the plan a shape (complexity), but doesn’t determine size. Estimates provide insights into the complexity of a project. But they are not fixed determinants of the final size or duration. What’s the last time you planned a 3hour trip in rush hour and your navigation tools estimate was accurate?
Human nature behind certainty and planning
Running a business is hard.
Running a successful business is very hard.
Running a successful business well is extremely challenging.
If the business was a hive mind AI, capable of operating with complete knowledge in one brain, all these problems would go away. It’s the separation of specialised knowledge that causes the need for sync meetings, roadmaps, plans and documentation.
The reality is senior management probably have no clue what or how you are doing work. As the people responsible for keeping the lights on, continuing to operate with zero operational knowledge is how you run a business into bankruptcy.
The purpose of roadmaps and estimation asked of your engineering and product department is to carry over a level of understanding and confidence to the business stakeholders. That is, without having to completely copy the collective contents of your brains.
Sigh.
And I’ve seen countless brain dumps of that nature.
Only to get ignored.
Don’t get me wrong. They usually contain all the necessary information.
But not for someone that lacks context.
I’ve written quite a few myself.
It feels bad to see the effort wasted.
6 Human Needs—Formula for Success
According to Tony Robbins our psychology balances itself chemically around 6 core needs:
1. Certainty: assurance you can avoid pain and gain pleasure
2. Uncertainty/Variety: the need for the unknown, change, new stimuli
3. Significance: feeling unique, important, special or needed
4. Connection/Love: a strong feeling of closeness or union with someone or something
5. Growth: an expansion of capacity, capability or understanding
6. Contribution: a sense of service and focus on helping, giving to and supporting others
The simplest way towards a successful enterprise is following a simple formula:
Grow by Contributing to others. Connect with your clients, stakeholders, colleagues by helping them increase their own self sense of Significance (Raise them up!). You do this by providing value in areas where they are uncertain and they will reciprocate by giving you safety—Certainty (money, status).
Now let’s use that formula to formulate our statement in the context of engineering leaders providing estimates for a roadmap:
You will Grow as leader by contributing to the success of your business stakeholders and users (their Significance). Figure out how to create value, so they will become better at their identity (ie. being a great accountants, profitable owners, founders, etc.). Make it about them.
They come to you out of uncertainty, fearing failure or chaos, to better plan their future and possible contingencies if they continue on this path. There seem to be many path of going about everyone’s quarterly plans. They want to connect with you, via estimation, to absorb the confidence your certainty—as the expert— provides them about the company’s engineering and product future. Continued success will provide certainty and (your) significance to you and your team in the form of salaries, recognition and bonuses.
How can you be sure the estimates are knowable?
Following the formula above, we can quickly find a few problems. There are a few paths through the conversation that involve effort but fail to provide certainty from conversation alone. The worst thing you can do is to get stuck in a loop of meetings, week after week, debating estimations about a topic neither party is knowledgeable about.
The symptom is clear: we don’t know.
The solution is clear too: we need to create knowledge.
Unless… when it is not knowable.
Before slipping down a rabbit hole of #noestimates rants and anarchy management, you should ask yourself whether what you are asking is knowable.
Specifically:
“Is it possible to know this without building the project?”
“Is someone else’s estimate and confidence transferable?”
“Even if there is a best practice and industry standard, does it apply to us without additional experience?“
When the answer to all three of these questions are straight no’s, escalation is the next step:
“You are not going to like this. We might have to start without a clear end date. Why are we uncomfortable committing to this project without an estimate?“
This conversation is a stepping stone to explore the natural constraints that the stakeholders already brought to the table but didn’t communicate. I’m of the opinion that it is our duty as engineering leaders to have the necessary conversation skills, negotiation ability and soft skills to navigate this.
This is completely irrational and to be expected on every important decision.
But it can be learned. Let’s explore your stakeholders’ constraints in the next chapter.
Stakeholders have constraints prior to asking for estimates
No plan, idea or increment that reaches your engineering department has been created in a vacuum.
At the very least—all ideas are constrained by the current financial limits of the business.
You may not know what those are. There may be a subset of those limits that apply in addition only to your department. And the other teams you are collaborating with.
Ignoring these pre-existing constraints is very easy. You simply come up with an estimate in some ideal vacuum, plus the team’s experience. Such estimates are always useful.
Ever had a conversation that went:
Stakeholder: “Hey, could you estimate project X by early next week? You’ll find the initial business requirements in this document I shared with you.”
You: “Sure, no problem.”
<you provide the estimate>
Stakeholder: “No, that’s too much.”
You:
Such responses have nothing to do with your estimates. The response is communicating that your estimate, if made a forecast or reality, exceeded a pre-existing constraint.
This is the start of the useful conversation! But most engineering leaders give up here. Because this is when things get difficult and we stumble.
Keep reading to learn how to navigate it.
Conversation patterns that annoy vs. foster collaboration
☒ Annoying
“Can we do X?” → No. Provides no certainty.
“How can we do X in a month?“ → We can’t. Provides no connection.
“Is it possible to do X?“ → In theory yes, but not here. Undermines significance.
“Can you estimate all of this?“ → *sigh* Sure. False safety increases uncertainty.
“Can we learn how to… X?” → We’re too busy. Blocks growth.
“Could you help with…?“ → Put it in the backlog. No guarantees of contribution.
☑️ Collaborative
“Can we do X?” → How does that benefit our users? Focuses on contribution.
“How can we do X in a month?“ → There seems to be a risky event at the end of the month… Provides connection, opens the door to knowledge exchange.
“Is it possible to do X?“ → How much risk are we willing to bear? Talking about uncertainties openly diminishes their fear factor and enables innovation.
“Can you estimate all of this?“ → I’m trying to understand overall strategy. Would you be still be willing to do this project if it’s longer than X months? Gathers the pre-existings constraints before estimations are invested into. Increases trust, connection and certainty.
“Can we learn how to… X?” → This is on <person A’s> growth goals. Would you mind them to leading it? Fosters connections, accelerates growth and signifiance.
“Could you help with…?“ → Love to. Though I’m in the middle of something. Is tomorrow a bad time? Combines connection with certainty, while validating the other person’s significance.
Estimation gives the plan a shape (complexity), but doesn’t determine size
I have given a presentation on this topic recently. I managed to capture the pieces that evoked the most a-ha moments. Before we go into them here’s a few general observations.
Your stakeholders will likely be most emotionally attached to the most constrained resource they are concerned about or the one they control the most. Usually it’s the one they have the transparency of for consequences (ie. time by facing consequences of missing deadlines).
They will be leaning towards reacting harshly when you are trying to control that one constraint by proxy of providing an estimate that moves it. For example: When you have a stakeholders that values time, they are more likely to explode if your estimates causes force them to move their timeline.
This doesn’t mean the timeline cannot be moved. But it’s them that has to decide it has to be so. Definitely not you. And definitely not by proxy of estimates. This might sound esoteric, so here’s an example of a mortgage:
You have a budget of $400k and need to move within 6 months. You lose your current home in 6 months.
You look for houses, you find one. There’s just one problem. The agent tells you, you need to move 8 months from now, not 6.
How do you feel?
Now re-imagine the example by moving the budget up instead of time. But who knows what could happen in 8 months? Maybe they’ll find a buyer who offers more?
The estimations don’t expose the real structure of the plan—they expose how sensitive they are to fluctuations in the scarce resources. And that is complexity.
💬 Join the Discussion
I'm eager to hear your experiences and insights on estimation, roadmaps, and collaboration with stakeholders!
Share your tips, challenges, and success stories in the comments below, and let's learn from each other's experiences. Don't forget to tune in for our live discussion on Thursdays 5pm CEST, streaming on YouTube and LinkedIn.
Here is the previous one in case you missed it: