Retraining Ourselves

With that vision in mind, you can change the way you approach estimation to make it your reality. Perhaps not perfectly, and certainly not immediately, but you can train yourself to operate in more effective ways.

When Asking for an Estimate

Let’s start from the point of view of the person requesting an estimate.

When you ask for an estimate, what information do you give? Do you explain how the estimate will be used and what decisions depend on it? Do you discuss the accuracy and precision needed, and the desired direction of error? As we discussed in ​When You’re Asked to Estimate Something New​, these are things that the estimator needs to know to produce an estimate appropriate for the need.

Or do you assume that the estimator already knows this? Perhaps they’ve been told once. Or it’s “common knowledge” how we do this, here.

Do you even know how the estimate will be used? Are you, perhaps, stuck in the middle, relaying someone else’s request for an estimate? This is a tough position to be in, sharing the difficulties of both sides of a request for an estimate. Your job becomes one of facilitating the flow of information and understanding. If you can get the person needing the estimate in direct communication with those providing the estimate, you’ll save a lot of missed connections. You’ll still need to facilitate the conversation and help ensure that both sides get what they need. That’s easier, though, than being the conduit of information and trying to help each other understand the other’s needs without direct connection.

Verify a Common Understanding

First, make contact with the other person. What do I mean by that? I mean connect with them as a person, and invite them to connect with you as a person. At that level, we are all peers. How you start the conversation has a great impact on how the conversation goes. Offer them the safety to respond in a genuine fashion.

Making a request, and even describing the need behind the request, is insufficient for effective communication. Has the other person fully understood the request and the need behind it? How do you know?

When you simply make a request, you can’t be sure it was even received. If the request is acknowledged, you have an indication that it got there, at least in part. If the request is repeated back to you, then you can tell whether the words were heard. At this point you’re still not sure if the meaning has been conveyed. Human communication can be ambiguous, and the message may be taken to mean something other than what you intended.

When communications are going well, humans can share an understanding so intimately that complete sentences are unnecessary to convey the message with all of its subtle shadings. Until you reach that point, a dialog is a great tool for completing the communication. Note that in dialog, the emphasis is on understanding the other, and in discussion, ideas are set against each other to determine which is best. There is room for both, but if you’re trying to get alignment, then dialog is more suitable. Explore the terrain of the estimation request, including the background needs and the feasibility of understanding what is needed to complete the estimate.

Failing that, at least ask the question of what the other person understood from the request. Close the communication feedback loop.

Communicate the Need

Describe how the estimate will be used. With that use in mind, discuss the minimum accuracy and precision that will be helpful, and the desired direction of error.

If there may be multiple uses, talk about all of them. You may need multiple estimates. In fact, it’s highly likely you will.

Think of the Outcomes

All of this seems like a lot of work. Can’t you make a simple request and get an estimate? Perhaps you can, but perhaps not. Read on, and we’ll discuss some of the difficulties that can arise. More than that, think about what outcomes you’d like. What would you like to have happen?

Getting an estimate is not the outcome on which you should focus. The estimate is only a tool to answer some question or make some decision. That question or decision is in service to some larger goal. Focus on that larger goal. Shortcuts may be expedient in the moment, but are foolhardy if they undermine your larger goal.

When Asked for an Estimate

When you are asked for an estimate, how well do you understand the intent of the request? Do you feel you have a common understanding with the requester? Do you feel in a position to counter with other ideas, or even to ask for clarification on the needs or the planned use for the estimate? In other words, do you feel that you and the requestor are side by side, looking in the same direction at the work to be done and the goals to be achieved?

Often I notice that those who are asked for an estimate would answer “no” to all of those questions. That’s a strong indication that something has already gone wrong in the situation.

Make Contact

If the requester hasn’t made a person to person connection, it’s up to you to try to do so. That can be difficult if the requester is operating under the assumption of a strong power hierarchy. It’s an essential part of success, though. Find some commonality between you and them, whether it’s alignment on the business goals or a bit of humor. It may take multiple different probes to find that common ground if you don’t know much about the other person, but keep trying.

Explore the Need

Happiness depends on developing an estimate that meets the need. It’s important to understand that need. Get some idea of what decisions depend on the estimate. This will help you judge the accuracy, precision, and direction of error that will help make that decision possible. Explore the acceptable level of risk in the decision that depends on the estimate.

Deliver More Than a Number

Describe the unknowns and potential risks in the estimate. Discuss ways you can notice the level of risk passing the threshold of concern as the estimate ages. Make plans now to revisit the estimate based either on the simple passage of time or some indicator that you’re tending toward danger.

When Responding to an Estimate

How you respond when you receive an estimate affects both the current estimate and all future requests. Immediately, a congruent response helps you receive the estimate in the way it was intended. If you misunderstand the estimate, it’s the same thing as if the estimate was wrong. A congruent response gives you a better opportunity to discover and correct any misunderstanding.

Longer term, how you receive and use this estimate will affect your relationship with the estimator. Will you build trust or tear it down? At the same time, it will affect your reputation within a larger community. Word gets around, and you may gain or lose the trust of people you haven’t yet met.

Accept Estimates with Appreciation

Everyone likes to be appreciated for their work. Appreciation goes beyond saying “thanks” or “good job.” It includes a level of understanding of what went into the work and what value the work has. Without that, it’s a hollow statement and comes across as insincere. This can have the opposite of the intended effect.

When people feel appreciated, it strengthens the bonds between them and increases trust. It also makes them more likely to help wholeheartedly in the future. Both of these results indicate an increased reciprocal appreciation.

Explore the Details

Go over the estimate with the person delivering it. How was the estimate derived? What parts of it are confident and what parts are conjecture? What expectations have been included in the estimate? What circumstances could affect the accuracy of the estimate?

Successful use of the estimate depends on understanding it well. An estimate that proclaims “this project won’t be finished before July” is not saying “this project will be finished in July.” There are many ways to delay completion, and no estimate can cover all of those.

Avoid Misuse

Use the estimate to inform your plans, but do not assume that it is one. A projected finish date is not a guarantee or a commitment. It’s a stake in the sand, subject to revision as conditions change.

Remember that a good estimate is made with a particular use in mind. It hasn’t considered the universe of assumptions to support all possible uses. Don’t reuse an estimate without reexamining it and the assumptions behind it to see if it’s appropriate for the new use. A rough order of magnitude estimate for budgeting purposes is not useful for writing a fixed-price contract. An estimate of feasibility is not useful for judging the productivity of the development team.

If you have multiple needs, all is not lost. The effort done to produce an estimate may likely be useful in producing another, different estimate on the same work. Keep your notes, but redo the estimate. Let the previous notes inform the new estimate.