EP266: Ben Timpson: The ROI of Communication
Ben Timpson spent thirteen years in the Royal Navy before building a communication practice for CEOs and their teams. In this conversation, he and Jens Heitland discuss what military briefing culture reveals about gaps in how businesses prepare their leaders.
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The ROI of Communication
For thirteen years, Ben Timpson worked inside an organization built around a single assumption: that a leader's attention is the scarcest resource in the room. The military trains for this constantly. Before anyone briefs a general or an admiral, someone has already asked what that person needs to know, what they can afford to ignore, and what decision they are actually walking toward. Nothing reaches the top unfiltered.
Business rarely works this way. Executives receive information the way it arrives, raw, layered, and shaped more by the sender's convenience than the receiver's need. Ben described CEOs waking at four in the morning to answer a thousand emails before the day has properly started. Not because the decisions inside those emails all matter equally, but because nobody upstream has done the work of separating what matters from what does not.
The pattern he pointed to is not a communication problem in the usual sense. It is a design problem. Teams push information upward because sending a decision to the top feels safer than making one. Leaders absorb it because refusing feels harder than accepting it. Over time, this becomes the default operating rhythm of an organization, and rarely does anyone name it as a choice.
Ben's military background gave him a different default. Before any senior person walked into a negotiation or a diplomatic meeting, someone had already asked what the other side cared about, what they were sensitive to, and what outcome the meeting actually needed to produce. That preparation is not about controlling the leader. It protects their attention long enough for them to use judgment on the parts that actually require it.
The consequence of skipping this step compounds quietly. An organization that never builds this discipline ends up with leaders exhausted by volume rather than sharpened by clarity. Talented people spend their hours processing instead of deciding, and the gap between what they could contribute and what they actually get to contribute widens without anyone noticing exactly when it happened.
Ben has since built training around teaching teams to do this preparation deliberately, in both directions. Junior people learn to ask the questions that shape a clean brief before it reaches a leader. Leaders learn to ask for that thinking rather than accept whatever lands on their desk. Organizations that adopt this tend to describe the same shift: a conversation that used to take twenty minutes now takes five, and the decision at the end of it improves rather than weakens.
This closely matches what I see across the CEOs I work with. Very few of them get briefed properly before high-stakes conversations. Most work from fragments, sometimes generated quickly and without the context that would make them useful. The gap Ben described in the military, and now closes in business, is not a technology gap. It is a discipline gap, and closing it tends to return far more than the hours it costs to build.
Timecode:
00:00 EP. 266_Podcast_Jens_Ben Timpson
02:53 Ben's Background & Bosnia
08:29 Preparing Leaders for High-Stakes Meetings
25:27 The Gift-Giving Empathy Story
27:54 AI's Impact on Briefing
35:10 The Briefing Course
45:01 How to Reach Ben
Guest Links:
Website: https://thebriefingcourse.com/index.html
LinkedIn: https://www.linkedin.com/in/bentimpson/
Transcript:
[00:00:03] Jens Heitland: Ben, it's great to meet you again. I'm so looking forward to our conversation because last time when we met, we have been in a conversation with a group of people, and you explained the difference between how the military is communicating and how it is in a business. And at that time I, I was thinking, but military, they're shouting at each other all the time.
[00:00:26] Jens Heitland: That's at least was my external perspective. So great to have you here, and let's directly dive into that point. So what's the difference between military communication and, like, management communication in organizations?
[00:00:39] Ben: Great to see you again, Jens. It's a really interesting point because the thing that I was talking to that group of people about was you would assume that communication in the military is very direct, shouty, and aggressive. But underneath that, in my opinion, the military is one of the most empathetic organizations when it comes to communication because people can be very direct. The key thing is that all the way through my military career, I was always taught to put myself in the shoes of the person I'm speaking to. When we're communicating up with a leader, I'd be thinking, "I've got to give him this message, but how is he or she going to interpret that, what decisions have they got to make off the back of it, and what pressure are they going to be under?" So even though on the surface it might look quite direct and aggressive, it's actually about understanding the other person. When you were talking about the difference between communicating in the military and communicating in business, I think that's actually what's missing a lot of the time in business because people don't have that same impulse to think, "How is my message going to land with this other person, and is it going to help them do their job, or how is it going to make life difficult for them?" For me, that's one of the key things I took from my military career, which leads into what I do now: how can we bring some of that empathy into our communication to help other people do their job better?
[00:02:17] Jens Heitland: It's a fascinating topic. That's why I definitely wanted to have you on the podcast, because I think communication is on one hand so easy because we communicate every day. We almost cannot not communicate. But on the other hand, it's so difficult, specifically when it comes to an organizational context.
[00:02:38] Jens Heitland: So let's go back to how you got started. First, your part in the military, but even further, what was the spark that got you into communication and thinking about these topics?
[00:02:52] Ben: Well, my
[00:02:53] Ben: my journey into the military is actually a very simple one: pretty much all my family have been in the military. I had no intention of going into the military at all, but then I got to 18, and there's obviously some part of my genes or brain that switched on and said, "You're joining the Royal Navy."
[00:03:09] Ben: So I did. I spent the early part of my career in a traditional way, navigating ships and that type of thing. The thing that really got me interested in communication was when I was 25 and got the opportunity to be a spokesperson for a peacekeeping mission out in Bosnia. I hadn't really had much experience with it, but one of the beauties of the military is sometimes it drops you into a new situation and says, "Go." That experience in Bosnia was a revelation for me. I had the time of my life and absolutely loved the job. I loved thinking about communication, audiences, and writing speeches. For me, that was a pivotal moment where I thought, "This is what I want to spend the rest of my career doing." I was very lucky that for the rest of my military career, I managed to pull myself into jobs focused on communication.
[00:04:09] Ben: The military sent me away for a year to study strategic communication. By the time I'd been in the military for 13 years, I'd built up quite a bit of experience. I made the decision that if I was going to continue a career based in communication, I was going to have to leave the military, because at some point you have to go back and do other jobs to build up your portfolio. So I left and did something very different than most people do when they leave the military. Most people go into a secure job in banking, insurance, or construction, but I went straight in as a freelance speechwriter for different companies and CEOs. The beauty of that—even though it was scary and felt risky at the time—was that because I was speaking to all these different CEOs in various industries, I got snapshots of what life was like for senior leaders in different businesses. It comes back to what we were talking about at the start.
[00:05:17] Ben: What I saw in the military was a culture of being very focused and disciplined whenever we spoke to a senior leader. If I was going to present a decision to them, I'd think very carefully about what I was going to say, try to cut as much noise out as possible, and present it in a very focused way so that they could make a good decision quickly. In the business world, I saw that discipline quite often lacking. You'll know this, Jens, with the amount of CEOs you speak to, but a lot of them are overwhelmed and have to process so much information every day. Often they're brilliantly talented people, so they're very good at doing that, but it's still not a positive situation to operate in. What I thought was, can I bring some of that military empathy and discipline into the business world? I created The Briefing Course, the theory being: what if I could boil down the stuff I did in the military and put it in a package for business leaders? That was the theory, and I've spent the last two years thoroughly testing and running it out as a product. I've been surprised and delighted with how well people have received it. People really connect with it, and particularly in this age of AI where it's so easy to generate information now, it's becoming more important
[00:07:04] Jens Heitland: Yes.
[00:07:06] Ben: to develop that rigor. That was a long answer to where I've come from and how I think about communication. Essentially, I come from a military background regarding communication, but I think that's turned out to be quite an advantage with the world the way it is today.
[00:07:29] Jens Heitland: Let's go into something specific. You mentioned that you were responsible for communication topics in Bosnia when you were young. What are situations like this? Because if you are in a company like I was over the last decades, you're in a safe environment. You don't need to worry except when there's a PR crisis, but the rest of life is pretty easy and you just go with the flow.
[00:07:57] Jens Heitland: Comparing this to an environment like Bosnia or other situations where you have been, what are the specifics, and what are specific situations where you needed to sort things out and said, "Now I really need to gather my thoughts to enable the best possible decision for someone that needs to take a really risky decision"?
[00:08:28] Ben: To give you a general example—
[00:08:43] Ben: which is not that different from what you see in the business world—it's whenever you are preparing an admiral, general, or politician for a serious meeting, whether it's a negotiation or something similar. I frequently had to do that, especially at the end of my career, because I finished in a strategic engagement role focused on promoting UK interests abroad. That meant I had to prepare senior people for meetings both in the UK and abroad.
[00:09:07] Ben: The consequences of those meetings were often pretty profound for UK industry. There would be huge defense deals riding on them, as well as diplomatic aspects where making a mistake and offending the other side could really mess things up. That was a great example of where I had to develop this skill because even though a meeting is crucial and huge things might be riding on it, the reality is you might only have ten or fifteen minutes to prepare someone. Their responsibility is so broad when they reach those key roles that they really don't have detailed knowledge on every specific item.
[00:09:52] Ben: You're presented with the challenge of how to use those twenty minutes to protect that person and our reputation when they go in, while getting the job done so they actually focus on the things that matter. I'll be honest, Jens, that's not something I always got right early on. But the beautiful thing about the military is they let you know when it's not right. I had my head ripped off a few times; it's painful and embarrassing, but I'm grateful for it now because senior leaders made it clear how I needed to operate.
[00:10:38] Ben: This is how you need to connect with people. That's an example of a real learning experience and the foundation of what I do now.
[00:10:49] Jens Heitland: I imagine you are almost wargaming for yourself. You need to look into all the different parties involved, the political influences, and the personalities. Especially in your context—an international environment—a UK person is different than a person in the US or Germany.
[00:11:17] Jens Heitland: Even though we think Western cultures are similar, they're all different with their culture. You have worked with the Middle East or South America, where it's different again. While the base might be similar, in the end, you really need to prepare someone on the spot.
[00:11:42] Jens Heitland: On one hand, it's pressure for that person, similar to a CEO who needs to make decisions daily or hourly, and then for you, being able to create a briefing for that person to make that decision. What is fascinating to me is that this isn't often the case in business. I have worked with CEOs across the world, internally and externally, and most of the time they aren't getting a briefing at all.
[00:12:16] Jens Heitland: If someone is doing something, it's half-baked with AI,
[00:12:23] Ben: Yes.
[00:12:24] Jens Heitland: and it's not prepared. That's a missed opportunity, specifically in business and regarding the brain drain of an executive with huge responsibilities. I was reading the other day about a CEO who gets up every day at 4:00 a.m.
[00:12:45] Jens Heitland: to read 700 to 1,000 emails and answer them.
[00:12:49] Ben: Yes.
[00:12:50] Jens Heitland: That's crazy.
[00:12:51] Ben: It is crazy. It's not a good use of their time. You're using all that talent and experience to process noise, and how much energy is left over for them to focus on what matters? The trouble comes back to the fact that these CEOs are phenomenal, bright, and talented people who work all hours of the day, so it can appear as if they can just deal with it. But you have to see them for what they are: a decision-making machine. You should be thinking, "How do we apply all of that to the key things that matter rather than using them to process noise?" To return to your point about people not getting a briefing, you're absolutely right. I see it everywhere: when people prepare a leader for a key negotiation or board meeting, they give them the most basic talking points.
[00:14:03] Ben: They say, "Here are some statistics, here are a few things you could cover." When you do that, you're shoving the intellectual burden upward onto them. You're saying, "You not only need to perform and land your message, but you also need to work out what should be left out, what should be put in, and what really matters." What I was trained to do in the military—and what I think is priceless—is to get your team to do some of that intellectual work. Returning to the example of preparing people for a big international meeting, my job was to ask a huge number of questions.
[00:14:51] Ben: What is the other side's background? What appeals to them? What are they worried or sensitive about? What can't we talk about? What's going to grab their attention? Working through these questions and drawing information from different people could take days.
[00:15:10] Ben: The key is using my judgment to decide what we are actually going to do in the meeting and making that as clean as possible. When you hand it to the leader, you say, "This is important, this is important, and this is important. Therefore, in this meeting, say this and avoid that." They don't have to follow it; they can completely disagree and say, "You've misunderstood this, and I believe this is the way to go." But you've initiated that conversation and allowed them to exercise their judgment directly. In simple terms, it's about getting your team to step up and do that thinking without nervousness. A lot of teams think, "This CEO earns millions of dollars and has 30 years of experience, so it's not my place to share my
[00:16:19] Jens Heitland: Yes.
[00:16:19] Ben: thoughts." Yet every CEO in the world is saying, "Please, I want your thoughts. Even if I disagree, I want you to join the conversation because it makes my life so much easier to have something to react to rather than being handed a load of rubble and asked to build something." Basically, Jens, I agree with you; I think it's really important.
[00:16:48] Jens Heitland: When we communicated over WhatsApp a couple of months ago, you explained how you work with a company and ran a workshop for them. It felt like a two-way street.
[00:17:08] Jens Heitland: One path is the executive team talking to the CEO or employees talking to team leaders. It works across all levels of an organization if you educate people. But it's equally about leaders learning to define what they need to make decisions, if I understood our conversation correctly.
[00:17:36] Ben: Yes. Done right, it's a virtuous cycle where teams ask themselves tough questions about what's important and what needs to be escalated, and the leader feels comfortable asking the team those same tough questions. The first time I experienced that was working in the Ministry of Defence. I presented a leader with something vague and gave the background. He came back to me and said, "No, I want to know exactly what we're doing here," putting me on the spot. The first time it happened, it was uncomfortable, but it was brilliant because he was inviting me to step up and provide the answers. You're absolutely right: it's a two-way street where leaders open conversations by saying, "I want more of your views and judgment when you pass things to me." Generally, the tools I provide also serve as great overall communication tools.
[00:18:57] Ben: If you're a leader using them, your communication becomes sharper too. When I deliver training, the focus is on upward communication because that's the piece missing most right now, but
[00:19:12] Jens Heitland: Yes.
[00:19:13] Ben: a lot of leaders love it because they take it on board and say, "This is how I should be talking with my team too."
[00:19:20] Jens Heitland: Yes.
[00:19:21] Ben: So when it works, it loops continuously.
[00:19:24] Jens Heitland: What is interesting—and not really talked about in organizations—is how you prepare a general or CEO. One part is the communication piece, but the other part is reading the emotional intelligence of the room.
[00:19:48] Jens Heitland: When I was around 25, I had the opportunity to be in rooms where I was far too young to be. A mentor took me aside after a meeting and asked, "What did you see?" I answered, "I've seen people..."
[00:20:15] Jens Heitland: He taught me: "This person was nervous. This person had a different agenda to get across." Since that day, I go into meetings observing the room with those eyes.
[00:20:36] Jens Heitland: People who have learned this skill use it, but many in organizations don't focus on it at all. When messaging is clear and packaged well, how do you address the invisible, emotional side when working with teams?
[00:21:10] Ben: It's phenomenally important to figure out a way to do that. Funnily enough, Jens, I had the exact same experience when I was young. When you're going through basic training in the military, you spend time on a warship, and for one day you shadow the captain to see what he does. He took me into a meeting, and I sat there and watched. Afterward, he asked me the exact same question: "What did you think? What did you see there?" Just like you, I said, "I don't know," because you're terrified.
[00:21:50] Jens Heitland: Yes.
[00:21:50] Ben: When you're junior in your career, your defenses are up, and you don't have human empathy turned on because you're scared. To answer your question, it comes down to preparation and awareness. In my training, I talk about understanding that when you're nervous and junior, empathy is something you have to actively engage with. I encourage people to prepare before entering the room by asking questions about attendees: What do they care about? What are they nervous about? What are they likely to engage with?
[00:22:46] Ben: What's their psychological home turf? If you practice empathy beforehand, you're already inside people's heads, so by the time you sit down, you know what to look out for. People don't often talk about or educate on this, but it's phenomenally important. Preparing a senior leader for a meeting is half empathy: understanding where the other person's head is at when they walk into the room.
[00:23:27] Ben: Are they nervous or angry? What are they there for, and is it aligned with our goals? It's easy to skip empathy and jump straight into details, but your words land on a canvas where someone has already told themselves a story. Whether you're a junior person adapting to a senior environment or engaging in any communication, bringing empathy back into situations where you naturally turn it off is critical.
[00:24:20] Jens Heitland: From a business mindset, this must be a huge growth driver for an organization. What you explained works in different meeting settings, but especially in big negotiations involving multi-million dollar deals and high-stakes political meetings.
[00:24:46] Jens Heitland: It's equally important even in a small sales meeting to understand the other side, the influences, and how to get your message across clearly.
[00:25:06] Jens Heitland: How do I get my team onto this?
[00:25:10] Ben: It doesn't have to take long.
[00:25:12] Jens Heitland: Yes.
[00:25:12] Ben: It could take 30 seconds to pause and ask, "Where are they at?"
[00:25:19] Jens Heitland: Yes.
[00:25:21] Ben: "When we sit down, how can I bridge that gap?"
[00:25:35] Ben: One of the most unusual tasks I had in the military while arranging diplomatic meetings was coming up with ideas for gifts. I hated it initially because the British military has a tiny gift budget. Other countries give extraordinary gifts, and we have to reply. Although annoying at first, it became a fantastic empathy exercise: "With a tiny budget, how can I show we understand them?" I arranged a meeting with the head of a Middle Eastern nation's navy. Research revealed a key part of his career was on training sailing ships.
[00:26:48] Ben: I bought a late 18th-century Royal Navy guide for boy sailors on eBay for a small amount. It was an amazing book with diagrams of knots. We had it signed by our representative and handed it over. It was magic because it demonstrated, "I get what you're passionate about." It was powerful, all from thinking about their situation and how to show understanding before moving to discussion.
[00:27:35] Jens Heitland: That's great. Those small things make a huge difference for relationships. Fantastic example.
[00:27:54] Jens Heitland: Let's talk about AI. People might ask, "You do speechwriting and communication, so why can't I just do that with AI?
[00:28:10] Jens Heitland: I drop in my idea and that's it."
[00:28:14] Ben: For the last year, I was worried about that too. Looking at training, AI hasn't improved communication with leaders; in many cases, it made it worse. Because AI makes generating information easy, leaders have more information shoveled onto them. Barry O'Reilly calls it the "processing pass-off"—passing the responsibility of consuming and processing information up to leaders. Then you hit a human bottleneck: a CEO answering 1,000 emails a morning. It remains crucial to teach people the discipline of communicating what leaders really need to know. Speed isn't the advantage; quality of decision-making is.
[00:30:21] Jens Heitland: Yes.
[00:30:22] Ben: I read a post where someone was delighted they reduced CEO briefing prep to five minutes. But is the CEO better prepared? No, you just saved yourself five minutes. Soon there will be a backlash where people demand real thinking for competitive advantage.
[00:30:57] Ben: People will ask how to make their team sharper than the competition. The answer isn't AI; it's getting people to think differently.
[00:31:07] Jens Heitland: Yes.
[00:31:08] Ben: Regarding speechwriting, I am not convinced AI will replace it, because of empathy.
[00:31:23] Jens Heitland: Yes.
[00:31:24] Ben: The secret to a great speech is deeply understanding the audience, which relies on human perception and asking the right questions. AI isn't funny, can't make me laugh, and lacks that human spark for an "aha" moment or genuine laugh. Speechwriters are safe.
[00:32:01] Jens Heitland: It's a tool you can leverage. I use it daily for many tasks, but I brief CEOs in specific contexts.
[00:32:20] Jens Heitland: When going into details with them, I need all the context. If text is written by AI without the ability to connect background dots during strategic planning or client pitches, it fails.
[00:32:56] Jens Heitland: It connects to empathy and people. Context must be in my head to wargame scenarios with the CEO. I can't pause to consult ChatGPT or Claude in front of them.
[00:33:19] Jens Heitland: That doesn't work.
[00:33:23] Ben: Yes.
[00:33:23] Jens Heitland: The way I connecting these dots stems from my experience across cultures, situations, and organizations, which isn't replaceable by AI.
[00:33:49] Ben: That's right.
[00:33:50] Ben: That's part of what makes you useful to CEOs. Competitors have access to the same AI models,
[00:34:06] Jens Heitland: Exactly.
[00:34:07] Ben: but competitors don't have access to Jens Heitland.
[00:34:10] Ben: Bringing something over and above AI provides an advantage precisely because it isn't leveled out by AI.
[00:34:32] Ben: AI is useful, but it accelerates thinking. If the core thinking isn't done, you accelerate vague thinking upward. If you make smart choices and feed them into AI, it's effective, but people must be educated on that first,
[00:35:05] Jens Heitland: Yes.
[00:35:06] Ben: otherwise you move quicker in the wrong direction.
[00:35:08] Jens Heitland: I agree 100%.
[00:35:10] Jens Heitland: Let's discuss The Briefing Course in detail. What are the scenarios you work through with organizations?
[00:35:18] Ben: I work bottom-up or top-down. Bottom-up means upskilling developing professionals to think clearly and communicate efficiently with leaders. I ask them, "Who finds it difficult to stand in front of the boss and deliver a message?"
[00:35:47] Ben: A lot of people
[00:35:50] Jens Heitland: Yes.
[00:35:50] Ben: are nervous about
[00:35:51] Jens Heitland: Yes.
[00:35:51] Ben: it. I tell them it's natural to feel that way under pressure, and I equip them with a toolkit for their next approach.
[00:36:11] Ben: It's not about turning people into automatons, but giving them tools to build confidence. Leaders notice the crispness and clarity. Top-down training equips leadership teams with tools so they can demand concise communication from their teams, giving the organization a shared language. Often leaders feel frustrated that communication takes too long or contains too much fluff; this framework helps them specify what they need. Conversely, teams often report struggling to make a connection or get through to a leader. I open the bonnet to look at what's underneath.
[00:38:03] Ben: It strengthens the link between teams and leadership. I work frequently with Chiefs of Staff because they bridge teams and senior leaders, finding great value in it.
[00:38:30] Jens Heitland: The return on investment must be phenomenal. In a 46-billion-dollar company with hundreds of thousands of employees, implementing a system like this saves significant internal costs.
[00:39:09] Jens Heitland: For sure.
[00:39:10] Ben: I have testimonials validating that. A client in the Canadian government was preparing her boss for a critical meeting when the other side attempted to cancel. Applying the communication principles, she saved a deal worth hundreds of millions of dollars.
[00:40:00] Ben: That's a clear example of how preparing leaders leads to better decisions and tangible results. Her testimonial video is available on my LinkedIn.
[00:40:25] Jens Heitland: Nice. Yes.
[00:40:25] Ben: It illustrates that when you put this in place, good things happen. It's a win-win.
[00:40:33] Jens Heitland: Even for listeners who don't engage directly, considering this topic will put them ahead.
[00:40:45] Ben: It's a massive blind spot
[00:40:48] Jens Heitland: Yes.
[00:40:48] Ben: for people. If you pay more attention, you're ahead of the game. Jens, you work with many CEOs and see how people communicate with them without much thought. Imagine the return when you apply focus. The military invests heavily in communication culture because decisions carry critical stakes.
[00:40:49] Ben: Business isn't life or death, but applying a fraction of this discipline yields strong returns.
[00:41:26] Ben: While investing in training is challenging in current markets,
[00:41:44] Ben: this provides a high-ROI intervention.
[00:41:56] Jens Heitland: As a CEO, I care about bottom-line cost savings and top-line growth. Effective communication impacts both.
[00:42:18] Jens Heitland: Organizations undergo frequent transformation cycles driven by communication.
[00:42:42] Jens Heitland: Poor communication causes organizations to lose people. Learning to communicate effectively works both ways.
[00:43:04] Jens Heitland: I find that fascinating.
[00:43:06] Ben: The transformation point is vital. In a small, static organization, established relationships compensate for poor communication because people understand unspoken intentions. During growth or transformation, those relational defaults break down when communicating new ideas to unfamiliar people. The military frequently moves personnel across roles, necessitating a shared code of conduct to align quickly. Organizations undergoing change must establish this early.
[00:44:43] Jens Heitland: Yes.
[00:44:45] Ben: Establishing this culture later is difficult.
[00:44:52] Jens Heitland: Fascinating topic.
[00:45:01] Jens Heitland: How can interested listeners reach out to you?
[00:45:11] Ben: Visit my website or message me on LinkedIn. I tailor services to each organization rather than offering standard packages.
[00:45:31] Ben: We start
[00:45:31] Jens Heitland: Yes.
[00:45:31] Ben: with a conversation to understand current friction points and structure solutions accordingly. Check the website or connect on LinkedIn to initiate a conversation.
[00:45:49] Jens Heitland: Ben, thank you for joining the podcast. I appreciate your focus on human conversation.
[00:46:00] Ben: And
[00:46:00] Jens Heitland: Thank you for your time.
[00:46:04] Ben: Great to speak with you, Jens.