I Learned about * From That: The Five Questions

For much of my career I functioned as a technical manager in the software industry, ranging from leading small development teams to serving as CTO for a division of one of the world’s largest technology firms. In those times I heard a LOT of presentations from bright and earnest people with terrific ideas: for new products, for new projects, for new initiatives. (And by the way, I made not a few of these pitches myself.)

After a time I noticed a pattern. Many presenters – especially younger ones – didn’t get this simple truth, that during a presentation managers are constantly thinking about two things: one, what decision do I have to make? And two, am I getting enough information to make the decision?

After all, that’s what managers get paid to do: make decisions. So above all else, your job in presenting is to tell – not hint, tell – the manager what the decision is. (I hate guessing what it is I’m supposed to decide.) That should be on slide 1 and on the last slide, and maybe sprinkled about the presentation.

So: be explicit about the decision: “we should buy Acme Industries.” “We should replace this database sooner rather than later.” “We should hire more people.”

Now as far as the second part, what sorts of information should you provide your manager?

Answer the Five Questions, and you’re off to a good start.

Question One: What is it?

What are you proposing? Tell your manager precisely what it is you’re suggesting doing, in as much detail as you think he or she needs to make the decision and no more. Don’t skimp and (and this happens much more frequently) don’t inundate your manager with details. The more detail you have, the more likely you are to find yourself at the bottom of a rathole with no hope of ever emerging. Your manager probably doesn’t need to know the details of all the error codes returned by this or that API.

Knowing how much information to supply is tricky and depends as much on the manager’s personality and interests as upon the merits of the proposal (and also, how much time you have: if your meeting is set for one hour, don’t waste it all on Question 1). Be smart and disciplined in your presentation.

Here’s a side tip: maintain control of your presentation. Your manager may think that he or she wants to know all those error codes, or some other details (or someone else in the room may ask). Try hard not to go there. Stay focused.

After all, you’ve got four more questions to answer.

Question Two: Why is it Good?

Why are you suggesting this idea? Why do we need it?

Specifically, what value will this thing whatever it is bring to us, to our organization, and/or to our company?

Will it save us money? Bring us a new revenue stream? Allow us to execute on our strategy quicker or more efficiently? Be as quantitative as you can: ”deploying this software will save us 20% year over year starting in 2022” or “implementing agile methodology will allow us to respond in days rather than months to new market opportunities.”

Question Three: Where Does it Fit?

I get it. It’s good. But we’re running a business here and we’ve already got stuff.  

Where does this idea fit in our ecosystem? If this is a new software package, how do we integrate it with the software we already have? Is this replacing something we already have? Or is it something new? (Please, please show me a picture.) What do we have to do connect it to what we’ve already got? Does it conform to our enterprise standards and/or generally how we do things? How much do we have to change our existing stuff to make it compatible with the new thing?

How do users use it? What new things will they/I have to learn? Who’s going to feel left behind? What’s your transition or change management plan? Do you anticipate resistance to your project once it starts? How will you handle it?

Question Four: How Much is it Going to Cost?

It’s not just the procurement costs, that is, the capital or operating expenses I’m going to authorize to be shelled out, although I definitely need to know that. How many people do I have to assign, and for how long?

And: What am I not going to be able to do because I’m doing this? It’s amazing how many projects sound just wonderful in isolation but then lose some of their luster when stack-ranked against other worthy proposals.

Question Five: When Will It Be Done?

How long will all this take? Is this a very straightforward, well-bounded project, or is this likely to be one of those projects that goes on, and on, and on? Make no mistake, I’m going to hold you to this, and while I understand projects slip for good reasons sometimes – bugs, key people quit, dependencies fall through – I’m expecting you, to the best of your ability, to make good on your schedule promises.

It’s not just about you. As a manager I have lots of other projects under way, and I may want to know, for example, when the resources you’re using will free up for another project.

[EDIT]: SteveB’s Question!

My pal Wes Miller reminds me that Steve Ballmer’s favorite question was “If we build this, how many zeroes does it add to revenue per year?”

Easy, Right?

If you can answer these five questions, then I guarantee we’ll have a productive conversation – no guarantee, however, that your proposal will be accepted. But I’ll come away feeling I had enough data to make the decision.

Oh, and …

One other thing: if I ask you a question to which you don’t know the answer, just say you don’t know. And – key point here – then say you’ll find out. Not knowing is understandable, but you need to always follow up.