Answering Big Questions in Big Meetings

Mike Shannon
The Startup
Published in
9 min readMar 2, 2020

I’ve been getting my face ripped off by big questions in big meetings for a solid decade now. My weak sauce rambling replies have garnered every type of reaction from, “just answer the f****** question” to “your baby is ugly” to “I like your partner’s answer better than yours” to “do you even have a clue?”. I’ve wasted a lot of generous people’s precious time honing my learning curve here. While I’ve yet to reach perfect mastery, I’m happy to share what I’ve learned in this category, and how improvement progresses across three phases:

(BTW — everybody at every level has a “big meeting”. From the student interviewing for the internship to the Fortune 100 public CEO on a quarterly earnings call. You know what “big meeting” means to you.)

1.) Answering a big question: “feelings” or “data”?

Both.

I’m instinctively a feelings guy. Ask me about a number and I’ll tell you how I’m feeling. My co-founder & CFO, Nick, is a numbers guy. Ask him how he feels and he’ll tell you a number. We’re both providing you with an incomplete answer when we do that. Over the years, out of sheer survival necessity, we’ve worked to improve ourselves by navigating closer to the balanced center of that “Feeling” <> “Data” scale.

While the following approach applies equally to “what’s going right?” as “what’s going wrong?”, this article will be geared primarily towards the latter.

When asked a big question in a big meeting, here’s a simple outline for providing a full response: inform on the available data | educate the audience on how to interpret the data | add my personal feeling & experience-based perspective | conclude by providing a corrective action step.

When it comes to the order, as much as I love my feelings, I’ve slowly recognized the distinct advantage of starting with the data first. This is for two reasons:

First, to squash the immediate skepticism that I may not actually know the data. No matter how many hours of hustle & grind, if I skip this step, I’m vulnerable to appear incompetent or even irresponsible in my area of ownership.

Second, if I start with my “feeling”, it presents as limited bias. Whereas if I start with the data, my “feeling” presents as expansive domain expertise. That subtle shift of the order in which I present my response makes a huge difference in the productivity of the given dialogue.

I probably won’t nail these four points the first time a new question come up, and that’s OK. Whenever a gap is exposed in my ability to fill any of the four components of a full answer, that’s an opportunity for me to improve for the next time (failing to do so would not be OK next time).

Fortunately, I typically have immediate assistance available for filling that gap.

2.) Becoming the driver of the next question.

8th grade Mike & the Principal

I’m tired of sitting in the Principal’s office with my tail in between my legs. I spent enough time there in grade school. The aforementioned approach to providing a “full answer” allows me to shift the dynamic from interrogation to conversation.

A full answer becomes a platform on which to direct specific advice-seeking questions. In doing so, I bring my interrogator over to the same side of the table to problem solve with me:

I’ve been wildly fortunate to work with and for some of the brightest, most accomplished individuals in my field. I’m often asked about how they add value. The #1 realization I’ve made is that the onus is on me to dig into them for the value-add. The brightest mind in the world can’t help me if I don’t provide an informed foundation for the dialogue. Specific questions, asked on the foundation of solid information, is how I dig for insight-gold with the folks around me.

I am the one responsible for driving this value-add process, which actually begins well in advance of the big meeting.

3.) Making it systematically easier on yourself next time.

My routine reality these days at Packback includes a Monday AM executive team OKR review to launch the week, a weekly RevOps analysis to wrap up the week, systematic weekly board of director updates/Q&A, six bimonthly board meetings reviewing a 70 page deck, and individual + team meetings mixed in between. While I spend an increasing amount of time as the questioner, I still spend a whole lot of time as the recipient of big questions in those big meetings. I’ve been told that our “tight ship” sounds treacherous for me. Yet I’m sleeping better than ever these days. Here’s why and how:

I don’t want to merely ace the interrogation. I want to drive the continuous dialogue in a manner wherein I’m in command. I expect my teammates to do the same. Here’s how I think about designing my command center:

  1. Black box → glass hood
  2. Consistent “spot the difference” picture, weekly.
  3. Pre-paint the first layer of the question tree
  4. Identify the common culprits.
  5. Define my course-corrective “levers”

I’ll explain the strange terminology:

1.) Black box → glass hood:

Make the available data transparent and communicated systematically with the necessary stakeholders. I’d much rather be over-transparent with all the ugly spots showing than to have a confused board, direct report, or manager (Ray Dalio refers to this as “radical transparency”).

The first step to operating with a glass hood is of course figuring out which metrics & data actually matter. Here’s a trick — don’t start with “metrics”.

Metric is a scary word that causes wrinkles, grey hair, and daytime drowsiness. Tell a story. Here’s the type of story you want to tell:

“I’m going to [destination], I will get there by [ABC pathways], and I will know whether I’m on or off course by [XYZ information]“

Now fill in those blanks with a specific number. You just tricked yourself into deciding on the metrics to track! (and yes, I just described OKRs)

2.) “Spot the difference” picture, difficulty level: Super Easy

Remember those “spot the difference” picture games? Think of the presentation & organization of your data like a game of “spot the difference”. Except in this case the goal is to make it super easy for the audience to spot what has changed. In order to do so, you want them to follow the same complete picture each week.

You do not want to paint a numbers collage and leave it to the audience to decipher the meaning. If the whole frame, organization, and order of your “data picture” changes dramatically week to week, it’ll be impossible for the audience to decipher the difference and you’ll waste a load of time in data clarification.

Consistent picture framing will gradually train your audience on what they’re observing each week. This expedites the big meeting right into the actionable dialogue around “what’s different” when something moves ahead or behind track.

Depending on the category, I typically want the data to include three depictions:

Ideal “pace”| Actual| Last Week

Ideally, the consistent picture guides the viewer’s eyes sequentially through the answers of their logical mental question tree:

3.) Pre-paint the question tree.

80% of the questions you’ll receive are predictable, and the first layer is always the same whether speaking to your investor, manager, or seven-year-old niece: “Why?”

Answer that question before it’s asked. To do that, you have to spotlight the information about the most likely causes.

4.) Define the common culprits.

“We’re 10% behind [goal/metric]. The data points that primarily contribute to this metric are [A + B + C]. As shown here, C is the current under-performer. Factors that typically contribute to C include[C1 +C2 +C3]”

…that’s how an an effective answer to a big question in your big meeting might kick off in the “data informed” and “data interpreted” steps. It’s a bit more exciting, however, to think about the adventure story at play here.

The culprits tend to be pretty common. Call them out. Catalog them somewhere. Then simply ask yourself, “hmm, which villain is most likely to blame? Lord Voldemort? Rita Repulsa? The Joker?” These same villains tend to break out of jail time after time. Our job is to investigate which one is to blame, and then decide on a corrective action to put them back in their place.

“Was it the Joker?” “No, he was not in Gotham yesterday.”
=
“Was it dials? No, the data shows that we are ahead of pace on dials.”

So on & so forth until you’ve narrowed down to the most likely culprit. That gives you the defining focus for selecting your course-corrective action, which brings us to #5.

(P.S → if & when you reach a scenario where none of your “common culprits” can be blamed, move fast & celebrate! You now have the opportunity to add a new culprit to the catalog, which in turn expands your future domain expertise/model/playbook when you do figure it out.)

5.) Know my course-corrective “actions” (aka “levers”)

So how do I put the culprit back in jail? There’s always an action within my control. I might not always pick the best one, or execute it perfectly, but there’s always an actionable “lever” to be pulled, and it’s my job to decide which one(s) to take.

Remember from “becoming the driver of the next question”, even if I don’t know the answer, that’s a perfect opportunity for me to take advantage of the folks surrounding me by asking a specific question.

“Hey, I have this problem, caused by this reason, and I’m trying to decide on the most effective corrective-action to take. I’m considering X, Y, & Z. What do you think based on your experience? Is there an action I’m not thinking of?”

Helpful insight can be found everywhere: your board member, manager, direct report, or even intern. The key that unlocks their value, is in asking specific questions, which are better positioned on the foundation of a full answer.

As I refine this system, I make my life much easier. Check it out! With a system like this, by the time I get to the big question in the big meeting, I’ve already prepared much of the hard work. Now I’m free to spend time talking about my feelings, and asking you specific domain questions to help me decide on the best corrective-action.

Take command.

In reality, there’s much more at stake here than saving face in the big meeting. Organizational & career success, like a personal habit, depends on our ability to continuously increase the speed of course correction. As I like to phrase it, getting “back on the rails” and “into the green”. If you’re anything like me, you’ll fall off track, a lot. Your ability to answer big questions in big meetings is simply a preview to how effectively you’ll be able to take course corrective action back in the arena.

You deserve to make your life a little less stressful as you go through these cycles of course correction.

Don’t just sit sheepishly in the Principal’s office. Put the Principal in the audience of your command center.

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Mike Shannon
The Startup

CEO & Co-founder at Impruve. Formerly CEO & Co-founder at Packback.