Save Time and Accomplish More by Asking Better Questions

From Scot MacTaggart, creator and host of The Pitchwerks Podcast, The Werkshop helps readers to scrutinize and practice a different skill every month, focusing on pitching and presenting to new customers or investors.

One of my many shortcomings is that I have certain beliefs that I tend to repeat over and over again, so if you have spent any amount of time with me, you’ve probably heard that I truly believe time is a lot more valuable than money.

If you believe that your time is more valuable than your money, we want to make sure that you get a good return on the investment you are making just in reading this piece. We’ll start with the normal process by which we engage with other people on any collaboration:

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  • Initial Concept. You think about working with someone on an activity. Maybe it’s their idea, maybe it’s yours. You’re not committed to doing this thing with this person at this time.

  • Exploration. In the sales universe, we call this the “qualification” step. The participants are trying to find out if they should commit to investing time and other resources in a collaboration.

  • Proposal. If the first two steps go by without uncovering objections, expect to spend a good amount of time on documents. You can’t sign an investment / sales contract / merger / co-marketing plan without having someone write up a plan based on the information gathered in the last step.

This list isn’t complete, but a lot of time can be spent just in these three bullets. Expect to spend time planning and executing these, but you must also communicate with each other to coordinate meetings, notes must be taken, team members must be included, a strategy has to be charted, and so much more.

Once all that is complete, the time after the proposal must be considered. Any number of things can happen - delay from bad timing, an unsatisfied partner that calls for more negotiation, or even a total split because you’re left wondering if the other party was listening during the exploration at all. Hopefully you’ve gone through a great experience where you can just sign the document and agree.

If we go back to the comparison between money and time, I doubt most of you have ever written someone a blank check. On the flip side, it is very likely that you write blank checks for your time on a regular basis.

Of course, the idea of spending your time more efficiently isn’t new. We all understand it, but have difficulty getting into the right mindset. On top of that, many of us do not have a concrete way to evaluate opportunities. When you have responsibility for other people, you have to protect the group’s resources so it can prosper, and that means that most proposals will result in a “no” response. In fact, strong leaders say “no” very frequently.

In order to have a more efficient Exploration step, let’s examine what kind of questions you can add to your repertoire. Perhaps these questions will unlock a “no” faster or unveil that exciting “yes” you’ve been waiting to hear.

So let’s reduce your time spending and get you working on more valuable tasks. By putting a process in place, we’re going to ask better questions, identify bad collaborations quicker, and only spend proposal, negotiation and project time on things that actually deserve your investment..

The next time you find yourself in the Exploration stage, ask these questions of your team AND the other party.

  • What is the perfect outcome? What is the likely outcome?

  • Why is this a priority? What happens if we don’t reach agreement?

  • Why now?

  • Why these participants?

  • What does each side know about the other? What mistaken assumptions do they have about each other?

  • How much trust can be developed between the parties?

  • What is each group going to be expected to contribute?

  • What other benefits - either in resolving problems or improving results - can be extracted?

For many of you, these new questions and a more patient approach will feel alien at first. Do yourself a favor and try it for just a month - I’ll have a new column out by then. It can be hard to develop a new skill, but if it keeps you from writing blank checks with your time, isn’t it worth it?

Scot MacTaggart