Impactful Communication: Douglas Squirrel On 5 Essential Techniques for Becoming an Effective Communicator
An Interview With Athalia Monae
Ensure commitments, use common, agreed-upon language, so everyone is clear on what we’re saying we’ll do. “Check twice and cut once” when making commitments so others can rely on assurances from you and your team.
In an age dominated by digital communication, the power of articulate and effective verbal communication cannot be understated. Whether it’s delivering a keynote address, leading a team meeting, or engaging in a one-on-one conversation, impactful speaking can open doors, inspire change, and create lasting impressions. But what truly sets apart an effective communicator? What techniques and nuances elevate a speech from mundane to memorable? As part of this series, we had the pleasure of interviewing Douglas Squirrel.
Douglas Squirrel coaches business teams on how to create and align on goals, discard good ideas that don’t fit the strategy, and deliver high-impact, customer-visible results. His Insanely Profitable Tech methods for rapid learning have been introduced at over 300 organizations on every continent except Antarctica, in industries from finance to biotech to music and many more. He co-authored Agile Conversations: Transform Your Conversations, Transform Your Culture, and has recently released Squirrel’s Tech Radar, a simple method for assessing any technology organization in under two hours with no tech background required. Learn more as Douglas Squirrel.
Thank you so much for joining us in this interview series. Before we dive into our discussion about communication, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
I was a tech executive — CTO, VP Engineering — at a wide variety of different companies. And I kept getting fired from each one.
I got fired in the nicest possible way, mind you. The CEO would tell me I’d built an amazing team and processes and that they didn’t really need me anymore. After being told several times to “go be wonderful somewhere else,” I decided I should be a consultant and plan for rapid improvements that make me irrelevant!
Can you share the most interesting story that happened to you since you started your career?
I sat next to the President of Lithuania on a commercial flight while on my way to coach leaders in a payments company in Vilnius. He’d just survived a tough NATO meeting so I let him sleep, but it was very interesting to see how he worked with his staff and a pleasure to compliment him on his humility once he woke up.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Humility. I had an executive role in a financial technology company, but didn’t know anything about the intricacies of our banking customers. So, I had to learn to ask clueless questions and admit ignorance to learn quickly.
Curiosity. I wrote a whole book (Agile Conversations) about how important it is to be curious, and why we tend not to be when it matters most! Just one idea from the book to share here: when you’re being curious, it’s important to ask genuine questions, like “what might be wrong with this idea and how could we improve it?” Our tendency when the chips are down is to advocate strongly: “we need to get on board and move this project along, don’t you think?” That’s not real curiosity!
Forthrightness. Sharing what you’re actually thinking or feeling can really change a conversation. As my friend Jeffrey says, if you’re bored in a meeting, try announcing that you’re bored — you can be sure it won’t be boring any longer!
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that we are all on the same page. How would you define an “Effective Communicator?” What are the characteristics of an effective communicator?
The key elements are transparency and curiosity: sharing what you think and feel, and being genuinely curious about what data others have. We all think we score highly on both when we make decisions, but the key tipoff that you’re communicating poorly is that you begin compromising on these behaviors. You think you don’t need to share all the information because it’s obvious, or we don’t have time to analyze it, and suddenly you’re wondering why you don’t have buy-in and alignment from others who have been left in the dark.
How can one tailor their communication style to different audiences or situations?
Ask questions slowly, to discover the other person’s story. When you rush to understand their actions before fully comprehending what they see, what’s important about it, what that means to them, and how they convert the observations to conclusions, beliefs, and actions, you don’t get the full story.
Can you provide an example of a time when you had to adapt your communication style to reach a particular audience successfully?
I had to learn the language of the CFO (capex, opex, cost of acquisition, cash flow) to be effective in budget discussions. Then I had to coach CFOs to ask good questions of engineers to help them plan and allocate resources! In both cases, learning the local “lingo” is just the first step; you also have to understand the story the other person is telling (see, for example, the narratives that good CFOs include next to every financial statement).
How do you handle difficult or sensitive conversations while maintaining open and effective communication?
My favorite technique for this is “say what you see.” For example, an executive I’m working with was blindsided in a board meeting by unexpected objections to a project plan he thought was already signed off on. I coached him on stopping the presentation and asking for the source of the objections, rather than plowing ahead. A “reset” like this gives you the chance to learn more about what others are thinking and feeling, rather than ineffectively guessing.
In your experience, how does storytelling play a role in impactful speaking? Why do you think stories are effective in communication?
Stories are the prime unit of communication, including about how software should work. We are programmed to remember stories much better than dry facts. Us tech folks are notoriously bad that this; we even have tools called “user stories” that are supposed to help us learn how people use our software, but we’ve managed to forget that such a story should be about a real person and have drama and excitement.
What are your “5 Essential Techniques for Becoming an Effective Communicator”?
1 . Build trust by slowly building up an understanding of the other person’s story using the Ladder of Inference: what do they observe, what’s important about those observations, what meaning do they attach, what conclusions do they draw, and how does that influence their beliefs and actions?
2 . Identify fears by looking for the normalisation of deviance (Diane Vaughan) — where do people routinely accept poor safety practices or skip quality checks, and what concern drives them, such as fear of missing a deadline or being embarrassed. Then don’t try to eliminate the fear, but mitigate it through joint design (see number 3).
3 . Don’t start with why when motivating your team; instead, jointly design the strategy (Roger Schwarz) by including all relevant people, asking genuine questions, seeking opposing and divergent views, and ensuring there’s a timebox and a clear decisionmaker. Dump “disagree and commit,” but ensure rather that your team is involved in setting direction all the way through.
4 . Ensure commitments, use common, agreed-upon language, so everyone is clear on what we’re saying we’ll do. “Check twice and cut once” when making commitments so others can rely on assurances from you and your team.
5 . Don’t “fire and forget” when delegating; ensure you have a “back briefing” (Bungay) safely in the diary so, within hours of agreeing on an outcome with your delegatee, you have a plan to review and a method for checking progress.
How do you integrate non-verbal cues into your communication? Can you provide an example of its importance?
Use them as clues not evidence. For instance, a red-faced person speaking loudly may be angry — or she may be frustrated, hot, or just trying to be heard over a jackhammer. When your brain prompts you with a conclusion based on someone else’s behavior, see that not as proof, but a prompt to ask a genuine question about what prompted the behavior.
How has digital communication changed the way you convey your messages? Are there any specific challenges or advantages you’ve encountered?
One advantage is that when you use text (Slack, Teams, WhatsApp, and similar) you get a record of the conversation that you can examine later. My co-author Jeffrey and I give many exercises in Agile Conversations for improving your empathy and curiosity by working on a transcript — for example, count the question marks in a conversation that went badly, and I expect you’ll find few (or none), and then you can work on improving your genuine-question skills. Text platforms, and now AI transcribers like Fathom, give you the record of what you both said so it’s easy to get started.
Public speaking is a common fear. What techniques or strategies do you recommend to manage and overcome stage fright?
Talk louder! Volume is a huge contributor to confidence, and if you consciously work on projecting your voice, you actually become more positive and assured.
What additional resources do you recommend for individuals looking to improve communication skills?
Read Agile Conversations and do the exercises! But more seriously, it’s very important not just to learn about conversational skills, but to practice them consistently. Write down conversations that you found difficult, revise to improve your curiosity and transparency, and role-play the improved version with others (or a mirror!)
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.
🙂 Help everyone learn to ask more genuine questions, to be more curious, and to be willing to change opinions based on new learning. That includes asking us tech nerds about what we’re doing and why, and not being intimidated by our technobabble.
How can our readers further follow you online?
Check out my work at https://douglassquirrel.com and my free community of tech and non-tech executives learning together about Insanely Profitable Technology at https://squirrelsquadron.com .
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!
About the Interviewer: Athalia Monae is a product creator, published author, entrepreneur, advocate for Feed Our Starving Children, contributing writer for Entrepreneur Media, and founder of Pouches By Alahta.
Impactful Communication: Douglas Squirrel On 5 Essential Techniques for Becoming an Effective… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.