Solving the Puzzle of Communicating Well with Execs

.... and anyone else who isn't on your project team.

Sep 06, 2023

Early in my career, I coordinated skunkworks projects and culture initiatives that required reporting on things that were happening "on the ground" to the Big Dawgs (ie. Execs).

To try and become good at this, I got my hands on any “executive communications” toolkit I could find.

Preparing for these meetings started to feel like I was Indiana Jones trying to crack the Dial of Destiny — I needed to solve this cryptic puzzle to report on my project in this magical way that got my team what they needed. It all felt so… hard.

But here’s the thing: execs aren’t mythical creatures that need to be spoken to a certain way, lest you disturb them and get chased out of the cave.

You’re dealing with someone who is relentlessly context-switching — and your ability to orient them to your topic efficiently is the unlock.

Georgia, on my team, offered a story to bring to life the opposite of what this looks like. :)

I started out my career in finance, and quickly learned that my safest space was Excel. After making a pivot into early-stage tech (and GoogleSheets, ugh, IYKYK), I continued to crush at making spreadsheets my primary personality trait.
Tasked with a simple analysis to inform a tactical business decision, I meticulously prepared rows of confusing numbers and notes. (Amanda here: if you’re just joining us now, this is something I like to refer to as The Backslide.) Armed & loaded for my exec meeting, I hopped on and confidently shared my creation. After that typical 2 seconds of awkwardly waiting, my trove of heinous cells appeared — and before I could get past a “can you see my screen?” — I was quickly halted:
“Can you summarize the top takeaways, and drop them in Slack?”
But what about my journey through my reasoning? I certainly didn’t have the highlights to drop in Slack BEFORE that riveting adventure. Just like that, a week of work was skipped over “until I was ready.”

The lesson?

With most stakeholders (especially execs), the value of your work is in your translation — not in your demonstration.

Sure, your peers might want you to show your work. But in most cases, and especially with execs: bring them up-to-speed efficiently, deliver your key insight, make your ask, and listen. Here are some quick tips for doing that.

1. Cruise in at the right altitude.

Anyone else live with someone who watches the Sci-Fi epic Foundation? Ever casually decide to join them, but on Season 2, Episode 4?

Yeah, good luck. You will frustrate yourself and everyone around you before retreating to your room to watch Love Is Blind: After The Altar.

Jumping into a complex topic with a flubbed tee-up evokes this same feeling (“wait, can we pause and rewind for second? What is happening here? Why is she turning green?”)

Instead of doing that – try this:

Envisage yourself a pilot.

I often think of altitudes. Depending on the other person’s familiarity with the topic, I typically start high, and then I slowly descend.

Some examples of what you’re covering at various altitudes:

Outer Space: “Why does this work matter?”

30,000 ft: “Things are going ok. Hitting some snags, but working through them.” 

10,000 ft: “Two work streams are struggling, and here’s what that could mean for the effort overall.” 

5,000 ft: “There are three things driving delays in those work streams. Here is what we’re doing [or would like to do] about them.” 

5 ft: “Here are the notes from our last meeting on this.”

Tarmac: “Here is what I need from you.”

There are a few things that are worth calling out about where to start:

If an exec is familiar with the work, but you need to orient them quickly to where you are — here is your descent: 30k —> 10k —> 5k —> Tarmac
- Don’t forget to land the plane. Hovering at 5k ft is a good update, but likely not the purpose of your 1:1.
If an exec is brand new to the work, provide a couple of Outer Space remarks, just to gauge alignment – “this culture initiative matters because we have a retention problem” — if you don’t have obvious agreement here, you’ll likely get stuck down the road. Pay attention.
Attempting to spend half of a 30-min meeting in Outer Space (exploring the “why” land) and then nose-diving to the tarmac will burn you alive. OK, that was unnecessarily terrifying, but it’s true. If you need to spend significant time aligning on the “why”, dedicate an entire meeting to that before cruising into next steps.
Preserve 5ft for the working team. Here is how I like to tee-up team-level discussions:
- Outer Space (because regular reorientation on the “why” is helpful)
- 10k ft (objective big picture on how we’re doing)
- 5k ft (actionable paths forward)
- 5 ft (who is doing what)

2. Guide Their Descent (Don’t Free Fall)

My first manager at PayPal gifted me a helpful framework for teeing up conversations at the right altitude, and it’s something I still use to this day.

The SCIPAB Framework:

When done well: each bullet represents no more than 2 sentences.

Situation: this is the current state; all facts (without controversy).
- “The Summers are hot in California.”
  - You want complete agreement here before proceeding.
Complication: something is hard or breaking.
- “Our Air Conditioning is running all day, and that’s really expensive.”
Implication: why does this matter? what is the consequence of not taking action?
- “If we keep spending money on our energy bill, we won’t be able to afford tickets to the F.O.R.C.E. Tour.”

Position: We need to do [THING].
- “We should install a whole house fan, and swim more often at our local pool.”

Action: This is what I need from you.
- “Can you please start calling around to get quotes? I’ll buy the kids new swim gear.”
Benefit: This is the benefit to you / our shared goal.
- “We love swimming, and 90’s hip hop. I think this allows us to get through the Summer in a way that gets us both what we want, reducing our power bill and lots of fun activities.”

Here’s a SCIPAB that tees up what we do at Garden Labs:

S: Scaling a startup is hard — and in a rapidly evolving emerging tech space, it gets even harder.
C: While most scaling startups would benefit from a COO, finding the right one is daunting. You’ll want to take your time to ensure there’s a fit across vision, skillset and values.
I: But most startups don’t have the time to wait. The cost of continuing to execute without focus, or scale without intention, is too high. Also, the risk of rushing in and hiring the wrong COO is tremendous.
P: Drop-in the experienced team at Garden Labs. We support on both the strategy and operations front, as coaches and doers, to help you tackle today and plan for tomorrow.
A: Let’s have a conversation to see if the fit is right, and feel free to chat with teams we’ve supported before to understand where we excel.
B: Get the benefit of COO-support now, gaining not only strategy and operations project support, but an experienced thought partner to help you find your ideal COO and spearhead critical company initiatives.

✨ Pro Tip: Use the SCIPAB framework to organize slides for a presentation. One slide per letter. ✨

Some helpful call-outs on how I use the SCIPAB:

Don’t. Forget. To. Pause.
- After Situation – you want the “yeah, that’s obvious” head-nods. Nobody should be tightening up here.
- After Benefit – you’ll want to solicit input. If you’ve done a good job of being really concise with Position, Action and Benefit – you’ve tee’d up the exec (or group) for a real discussion. Let it happen!
Don’t wander – get through the SCIPAB, avoid tangents.

Mastering the art of communication with executives is no sorcery - it's a skill that can be honed with the right techniques.

As with anything, the more you practice, the better you will be. Ultimately, when meeting with Execs, your goal is both to get through your message and to learn. Being really clear on your message will help you deliver it well, and will open your mind up to signals that you may be on the wrong path or have more to learn.

Amanda

Thinking in Quarters

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