II. Communicating Effectively as a Leader

Clear, concise communication from a leader may be the single-most important driver of an effective problem-solving culture. In this Section of the course, we’ll focus on four communication concepts that good leaders can and should deploy in their respective organizations to help promote a problem-solving culture:

  • Clarity– the simplest (dare I say, clearest?) summary concept here is never leave a meeting without everyone understanding who is responsible for doing what by when.
  • Use (and abuse) of digital communication tools– We live and work in a time when there is continuous proliferation of technology products to help facilitate communication. Without appropriate cues from leadership, many of these tools are often misused in ways that waste time and effort.
  • Meeting hygiene– The modern business meeting (whether face-to-face or digital), when not properly led, is another significant driver of wasted time and effort. Leaders using simple tools to help avoid this inefficiency can go a long way toward establishing a positive problem-solving culture and avoid wasting time.
  • Active listening– Possibly saving the “best for last”, or at least the most-often overlooked, for last— we’ll talk about the side of communication that is incredibly important but often ignored (or at least undervalued)— listening intently and actively.

   As with the other aspects of culture in this Part 3 of the course, these aspects of communication are often botched by leaders. When that happens, time that could otherwise be spent spotting and solving problems is wasted and organization members become frustrated and discouraged. While requiring intentional time and effort to establish, once implemented and role-modeled by an organization’s leader(s), these aspects of effective communication can unlock otherwise inaccessible problem-solving energy and organizational value.   

A. Clarity of Communication

Have you noticed a theme— especially in Part 3 of the course— about how human nature drives us toward behavior that isn’t helpful in problem-solving? Here’s another example of that phenomenon. Many of us are uncomfortable speaking directly. Too many leaders avoid directness and wind up either (i) not addressing important, but potentially uncomfortable, issues, or, (ii) speaking in vague terms to avoid “putting anyone on the spot.” This often leads to confusion and wasted time.

Take for example, a leader who ends a meeting by saying something like,

“Great, I think we did a good job identifying what needs to be done to fix our past-due problem in Peru. Now let’s go do it!”

That feels good to say, and great to hear—especially when everyone is eager to leave the room and get on with their day. However, ending a meeting with that sort of generality, without clarifying who is going to do what by when, often leads to the same group of people getting together several weeks later and slogging through the same issues again without making any progress.

A more skilled leader in a highly functioning organization, will end the same meeting by saying something more like this:

“Great, I think we did a good job identifying what needs to be done. I’ll go ahead and schedule time for us to get back together a week from today at this same time so that we can check status on the action items we identified.

 Just to make sure I’ve got all those down correctly, let me go through my understanding of who is doing what by then.

Julia, you agreed to find the customer past due data for Peru and come to next week’s meeting with some root cause insights on what’s driving it.

Juan, please check back with the product group and pin them down on when they expect to have that location-tracking technology embedded in their machines so we can more easily locate the units associated with past-due loans.

Elisa, please get with Paolo in Legal and come next week with a root cause analysis on why we aren’t more successful in enforcement actions on defaulted loans in Peru and at least 3 countermeasures we can deploy to fix the problem.

Did I get any of that wrong, or is there anything I’m missing?

If anyone runs into any questions or unanticipated obstacles, let me know. Otherwise, I’ll look forward to seeing everyone next week.”

Do you see the difference? In the second example, the leader is much more intentional about clarifying who is going to be doing what by when. Sometimes leaders—especially early in their leadership journeys– avoid these types of direct assignments or other clear communication.

There are a few reasons why leaders often aren’t very good at clearly communicating things like who is doing what by when. Some of the most common include:

  • They assume everyone knows. It’s generally a mistake to assume as a leader that everyone is thinking the same way you are. We’ve spent a lot of time talking about the value of diverse teams. The flip side of that value is that individuals’ differing set of background experiences and mindsets can create very different interpretations of the same set of facts. Never assume your interpretation matches everyone else’s. Plus, sometimes, believe it or not, not everyone (including you!) is paying close attention at every moment during a meeting. For these reasons, it’s always best to confirm understanding of major takeaways and who is doing what by when.
  • It’s the end of the meeting and everyone is tired and eager to get out. Think about your experience at the end of a class period. You’re eager to get on to the next thing, and you may even be a bit bored (never in this class, though!). Team members (and leaders!) often feel the same way at the end of a meeting and it’s natural to not want to extend the session by reviewing details like who’s doing what by when. Good leaders fight through that.
  • Some people are uncomfortable assigning accountability. No one wants to sound “bossy”. However, ensuring clarity about who is going to be doing what by when is a key function of leadership and team members generally prefer to work in an environment where expectations are clear and challenging than in a place where no one is sure what’s going on.

I’ve focused this section in the context of who will do what by when because that context is very common in problem-solving meetings. However, the importance of the general principle of clarity in communication has much broader application— especially in other situations where human nature sometimes leads us to fudge or avoid difficult conversations. One-on-one performance coaching is an excellent example. There will be times during your leadership journey when you see someone making a mistake or engaging in a behavior that is not super-great for the organization. In those situations, your role as a leader is to pull the person aside (without embarrassing them in front of others) and make sure they understand what they did wrong and how they can improve their performance/behavior in that area going forward. The clearer you are, and the closer in time you provide this coaching, the more effective you and your organization will be.

B. Use (and abuse) of email and digital communication tools

I began my professional career in the summer of 1993. The internet wasn’t a generally recognized tool in most workplaces. Soon after I started, though, my office introduced what was referred to as a “chat” tool that enabled members of the firm to communicate instantly with one another electronically via our desktop computers. Prior to that, if you wanted to ask a question or otherwise communicate with a colleague you had to either call them on the phone, hunt them down, or arrange to meet with them.

What a breakthrough! Especially as a young new member of a really old law firm, it was such a relief not to have to risk interrupting more senior lawyers and staff with annoying questions or worry about how and when I might catch them in the hall.

From there, of course, the rapidity of technological advancement in communication only accelerated. Soon after introduction of the internal “chat” feature, actual email was introduced, which facilitated digital communication with anyone else in the world with an email address. Today, of course, we have instant messaging (which looks an awful lot like the original “chat”!) as well as a variety of potentially highly productive tools such as Sharepoint® sites and Trello Boards® enabling problem-solving collaboration among disparately located team members.

Properly used, this all great. However, that nasty human nature of ours tends to lead us to abuse these various tools in ways that sometimes impedes problem-solving, and/or wastes time rather than saving it. A 2017 Harvard study found that an average employee checks emails 74 times a day and spends 13 hours, or 28% of the workweek, on emails.[1] These traps can be avoided, however, when a leader establishes an appropriate culture and leads by positive example.

1. The Traps

First lets look at some of the common traps

a. Moving the Monkey Syndrome. We’ve all heard the expression about getting the monkey off our back, or something similar. Too often, team members treat their email inbox as a collection of monkeys. Instead of directly resolving whatever issue the email (or other digital communication) raises, our objective becomes simply responding to the email and thereby (in our minds at least) shifting the burden of resolution onto someone else. Too often, responses motivated by moving the monkey off our back do nothing to resolve the underlying issue and only prolong the problem-solving process.

Take this classic example:

[Email in my inbox from Miguel @ 7:32 Monday morning]: “Hey, let’s get together for lunch to discuss the past-due problem in Peru.”

[My response @ 8:45]: “Yes, great idea, let me know when and where you want to get together.”

If my main objective is to respond as quickly as I can to all unanswered email in my inbox, I’ve succeeded with this response. I’ve also effectively moved the monkey off of my back and returned it to Miguel’s. However, I haven’t made as much progress on resolving the underlying issue (finding time to get together with Miguel) as I could have. My response will likely lead to the following continuation of the exchange:

[Miguel @12:30 pm] : Great, how about tomorrow in the sandwich shop in the lobby.

[Me @3:30 pm]: I can’t do tomorrow. How about Wednesday?

[Miguel @7:35 am Tues]: I’m taking Wednesday off. Friday?

[Me @10:00 am Tues]: Friday works for me, but the sandwich shop is closed on Fridays this month. How about the lobby Starbucks?

[Miguel @10:05 am Tues]: Fine, see you there.

While it would have required a minimal incremental time investment on my part at the beginning of the sequence, this matter could have been resolved much faster and more efficiently if my original response looked something like this.

[Email in my inbox from Miguel @ 7:32 Monday morning]: “Hey, let’s get together for lunch to discuss the past due problem in Peru.”

[My response @ 8:45]:“Yes, great idea. How about Wednesday at noon in the lobby sandwich shop. If that doesn’t work for you, I’m free for lunch either Thursday or Friday, although remember the sandwich shop is closed Fridays this month.

Similarly, if Miguel had invested a bit more time and proposed a specific time and place in his original note, the matter could likely have been resolved even quicker. The point is, investing a bit more time in the original note and/or response can save everyone time and effort downstream. This “extra time upfront” is hard to invest, though, if we’re in a mindset of wanting to get the email answered and the “monkey off our back” as quickly as possible rather than viewing the objective as resolving the underlying issue.

b. Prioritizing response velocity over quality. Closely related to the “Moving the Monkey Syndrome”, is the trap of prioritizing a quick response over a quality response. Often, digital-age expectations are that any digital communication must be responded to immediately. So, to both be seen as responsive and to get the monkey off their back, too many team members respond to emails without providing themselves a sufficient period of reflection. Maybe this is because they are receiving the email in a settings not conducive to deep thought[2]  or perhaps for whatever reason[3]  they simply refuse to provide sufficient reflection and therefore provide an incomplete, or worse inaccurate, response.

c. Making your inbox a proxy for productivity. There are certain jobs where it’s very easy to measure your productivity output. Many manufacturing units, for example, have very tangible key performance metrics around volume, quality and timeliness. At the end of any given day, it’s relatively simple to determine how many machines have been built.

However, for many “knowledge workers” measuring productivity can be a bigger challenge and in the absence of easily applied metrics many fall into the trap of using the status of your email inbox as a kind of internal metric for productivity. In this environment, clearing your email inbox by responding to email quickly (rather than completely) becomes a priority, and you can leave the office at the end of the day with a (temporarily) empty inbox and a false sense of accomplishment, when in reality all you’ve accomplished is moving a heard of monkeys and not solving any problems. [4]

Another danger in this approach is you become so obsessed with answering email that doing so dominates your day and you have insufficient time available to engage in deeper, more cognitively demanding work that actually leads to problem-solving. Hopefully, this sounds somewhat familiar from Part 1 of the course. A person who allows their inbox to dominate their day and time-management decisions probably isn’t deploying an intentional framework to identify and prioritize their Universe of Opportunities. They often aren’t thinking about email, or any other problem, as an opportunity to help them achieve individual or organizational targets. Nor are they likely to think critically about Urgent vs Important. More likely, they are just taking on one email message after another, trying to move the monkey off their back and chase the impossible dream of a cleared inbox.

2. Avoiding the Traps

So, now that we have covered some of the traps, what are the things a leader can do in order to create problem-solving culture that allows team members to avoid them?

a. Demonstrate a Commitment to Quality over Velocity. This is a bit of a catch-all and admittedly easier said than done. However, it’s important for a highly functioning organization to have a leader who’s not afraid to encourage team members to slow down and get it right. So, when you get that email response from a team member sent 9:30 at night with a rushed and incomplete answer, acknowledge their responsiveness, but urge them to put more thought into what’s been requested and respond when they’ve had a chance to access required data and/or spend more time in reflection.

b.  Clarify expectations on response time for requests. Here we go again with the importance of clarity in communication. One of the easiest ways for a leader to help team members avoid the trap of prioritizing velocity over quality is to be very clear about the timeframe in which a response is required to any request you send.

Everyone wants to impress, so when you receive an email request from someone – particularly if they’re higher in the organization, there’s an overwhelming urge to respond as quickly as possible. This is something supervisors often forget. Being somewhat of an advance planner, I would occasionally make the mistake of sending an email requesting information from a team member that I didn’t need for days or weeks later without clear guidance on the expected timeline. I wasn’t being mean. It just didn’t occur to me that the person I was requesting the information from would drop everything (including more important work) to respond to my request as quickly as possible. I failed to provide any insight that would allow the team member to assess the request on an Urgent/Important matrix and in the absence of further data, the team member assumed that it was both.

Even worse, the false sense of urgency would occasionally lead the team member to neglect consulting an important data set that was not immediately at hand and provide me a very quick, but incomplete or inaccurate, answer. The result was a lot of frustration and a problem not being timely solved. Again, hearkening back to our discussions in Part 1, leaders who clearly state the expected timeframe for response to their requests can help the team member whose response is being requested better distinguish where the request falls on the Urgent/Important matrix and provide a higher quality response.

c. Email boundaries and intentional calendaring. Intentionally calendaring certain points during your day to respond to email can help avoid the trap of defaulting to your inbox to manage workflow. As with most tools in this course, the effectiveness and viability of this concept will depend on the actual job function. If your job, for example, is to staff a Help Desk whose main function is to respond quickly to customer email requests, then only opening your email inbox at certain times of the day may not be realistic. For many jobs, though, setting intentional boundaries around responding to email and other communication technology vehicles can be helpful in ensuring that sufficient time is available for fully focusing on those requests as well as other means of problem-solving. When you can control such things, it’s helpful to designate your inbox-time at a point where you are most likely going to have access to sufficient time and data to respond to most requests in a thoughtful and accurate way. When that can’t be done….

d. Combine a quick response with a commitment to a more thoughtful followup. In an ideal world, you are only checking email and other digital communication tools in a time and place where you are in an appropriate space to consult relevant data and provide a thoughtfully reflective response. Realistically, though, that won’t always be the case. When you find yourself in a situation where you are being asked for input on a complex issue without time to reflect, then the best path is usually to:

  • acknowledge receipt of the request;
  • explain that further reflection is required to provide the level of response the request warrants; and

(3) set an appropriate time expectation for delivery of that response.

Often, a quick response acknowledging receipt of a request can be incorporated into a message acknowledging that the request will require more reflection or data than the receiver has access to. This combines the best of both worlds in the sense that you can impress the requester with a quick response (if culturally that’s helpful) while avoiding the trap of sending an inaccurate answer. One key to deploying this strategy is to ensure you have a personal organization and/or calendaring system to ensure you don’t forget to provide the response you’ve committed to.

C. Meeting Hygiene

Nearly anyone who’s worked in an organization will be familiar with the soul-sucking experience of sitting through a poorly organized meeting. Enormous amounts of time are wasted every day by leaders who have a vague sense that they should be meeting with a group of people, but who haven’t put nearly enough time into thinking through whom to invite to the meeting, how to conduct it or even why they are calling the meeting in the first place!

Avoiding the soul-suck, like many of the tips in this course, involves investing a bit more time planning to ensure better results. Specifically:

1. Make sure you identify (and communicate) the purpose of the meeting in advance. Every meeting invitation you send out as a leader should include the intended objective of the meeting, and if you use slides during the meeting, that objective should be one of the first slides shown. Everyone should be clear from the outset on why they’ve been asked to invest their time.

If the sole purpose of the meeting is to communicate something, consider simply sending a written communication. It’s certainly true that there are topics that are most appropriately communicated face-to-face. When this is the case, it’s important to ensure you have the smallest possible audience necessary to accomplish the desired outcome.

2. Invite only those people necessary to assemble a sufficiently diverse team to accomplish the sought-after result. There may be exceptional circumstances where you want certain people present for development purposes, but don’t fall into the trap of over-inviting “just to be safe.” In general, the larger the group of people, the more difficult it is to conduct a meaningful working session and the more aggregated time you’ll be wasting.

3. Have an agenda and circulate it in advance of the meeting. Many leaders fall into the trap of thinking that if they can just get the right group of people into a room and let conversation flow, then the objective of the meeting (whether they’ve identified one or not) will somehow magically be met. This very occasionally works out, but often, you wind up wasting people’s time[5] and deflating your organization’s limited energy reserve. Instead, invest time upfront to consider the purpose of the meeting, the people necessary to meet that purpose, and the activity in which they’ll need to engage in order to achieve that purpose. What specific questions need to be answered? What specific output needs to be produced? How can we best use the time allotted and the human capital we are pulling together to achieve that output?

4. Identify any data required for the meeting and provide attendees with advance access to it. If, to achieve the desired objective of the meeting, people will need to consider last month’s sales report, or another piece of data or analysis, make sure that is made clear in the invitation/agenda and ensure they have access to that data in advance.

D. Active Listening

The preceding sections focused on the importance of clarity in terms of pushing information out. Listening— or receiving information— is another equally, if not more important, element of communication. For some reason, our ability to actively listen sometimes diminishes as we gain more status and stature in life. Maybe it’s because as you get promoted to more senior positions you become more confident and (often falsely) sure of what you’re doing. “I’m now a [pick your title]. I no longer need to listen as attentively to those around me.” Huge mistake.

The ability to not just listen— but to actively listen— is a key attribute that the best leaders I’ve worked around never lose. On the flip side, the least effective leaders I’ve seen all tend to share an inability or unwillingness to actively listen.

What do I mean by actively listening and why is it so important? Consider interactions you’ve had with other people in the last few days. I’m guessing you can identify at least one interaction where the person with whom you were speaking seemed to have their thoughts elsewhere. Maybe they were nodding politely (maybe not), and perhaps they even threw in an occasional comment like “100 percent” or “uh-huh”, but it was pretty clear that they weren’t very actively engaged with you in that moment. (Maybe they were even checking their phone while you talked?)

Now, think of another interaction where the person you were speaking to maintained eye contact, asked you followup questions and seemed completely present, maybe even energized by the encounter.

Which made you feel better? Which person did you feel got more out of the interaction? Which person would you rather work with, or for, on a problem-solving team?

Active listening has several advantages. The first, and probably most important from the standpoint of leading a problem-solving organization, is that leaders who are active listeners learn more. We’ll talk more about this in a subsequent section on Respecting Those Closest to the Work, but actively listening to people at differing levels of the organization about their work and how they go about it is a hallmark of effective leadership. Second, when you are actively listening to someone, you are showing them respect and conveying to them that they are important to you— at least in that moment. Sensing that respect, the person you are listening to is more likely to reciprocate with heightened respect for you (and problem-solving effort on the organization’s behalf).

A few tips on how to actively listen:

  • Maintain eye contact. Nothing sends the message that you’re tuned out more than wandering eyes or worse— checking your phone.
  • Ask questions. Try not to interrupt flow unless you have to, but when the person you are listening to says something that you don’t quite understand, or that you want more information on— indulge your curiosity and ask.
  • If the context is appropriate, take notes. I’ll often walk around with a notebook for this purpose.[6] I used to take a lot of notes during business meetings and I found that I would rarely go back and refer to them, but just the act of writing things down— and the mental organization it requires— would help me stay better engaged and remember the experience.
  • Approach every interaction as an opportunity to learn and improve.

A quick story to illustrate the power of active listening. At the time I retired from Caterpillar Financial, our Chief Risk Officer was a guy named Zakhar Lifschits (no, I’m not making that name up). Zakhar was incredibly intelligent (he held a PHD in economics) and one of the nicest guys, and best leaders, I know. While relatively young, at least for his senior leadership role, Zakhar has already added tremendous value to our organization.

Zakhar told me a story once that occurred about 15 years ago, when he was just in his second year as a very junior credit analyst in Caterpillar Financial’s Moscow branch office[7]. A former boss of his had recently left the company for another opportunity and she, having an excellent eye for talent, reached out to Zakhar and offered him a position at a higher salary to join her new company.

Zakhar had all but made up his mind to jump to the new company, but he wasn’t sure. Fortunately, he had a really good relationship with the branch’s Managing Director, a guy named Anton Chadrin, and, even though Anton was two management levels higher than Zakhar at the time, Zakhar screwed up his courage, went into Anton’s office and asked if he had time for short chat. This was about 2:00 in the afternoon.

Anton greeted Zakhar and came out from behind his desk and turned the second guest chair in his office toward Zakhar so that they were both seated facing each other with nothing in between. Zakhar nervously and quickly explained the situation. As Zakhar now recalls the conversation, Anton never tried to talk Zakhar out of leaving Caterpillar and never even proposed a specific course of action. What he did, instead, was ask questions, listened intently to the answers, and asked more questions. Things like, “what motivates you?”; “where do you want to be in 10 years?”; “what are the things you enjoy doing both at work and outside of work?”

Through the course of the conversation, Zakhar sensed that although Anton was a very important senior leader in the company, he was also genuinely interested in Zakhar as a person and seemed to be trying to help Zakhar come up with a solution that would best serve him going forward— whether it was with Caterpillar or not. Here’s how I remember Zakhar concluding his story,

It was such an intense discussion— in a good way. It felt like even though I was a very junior member of the office who really hadn’t spent much time with Anton before, in that moment it felt like I was the most important person in Anton’s life. I’m not exaggerating. Another thing about Anton— he didn’t really like fluorescent lights, so during the daytime, he would leave his office lights off and just use the natural light from the windows in his office. This was wintertime and the sun sets early in Moscow, so although it seemed like we’d only been talking for about 10 minutes, at one point near the end of the conversation, I suddenly became aware that Anton and I were seated across from each other in a totally dark room. He was listening so intently to me— and so into the conversation— he hadn’t bothered to turn the lights on!

Zakhar decided not to leave Caterpillar and today is a member of our executive leadership team in Nashville, Tennessee.

Reflection Questions

1. Have you ever walked out of a meeting and felt your time had been wasted? What made it so ineffective? What would you have done differently if you had led the meeting?

2. Think of a time when you’ve left a meeting (or class) unsure of what you were being asked to do. Compare that to a memory of leaving a meeting (or class) where you were clearly asked to do something, perhaps difficult. How did you feel in each situation?

3. Can you think of a time when a digital communication or productivity tool designed to save time was used by you or someone else in a way that wasted time?

4. Think about the above questions and the root causes for why people fall into the types of communication traps described in this section. 5. Think about a time when you could tell someone in an authority position was actively listening to you. How could you tell? How did it make you feel?


[1]. Rapp an Jain, The Flywheel of Life and Leadership, p. 40.

[2]. i.e. just before ordering at the Starbucks counter

[3]. “My inbox is full and I need to get this monkey off my back!”

[4]. For a deeper examination of this phenomenon, see Newport, Deep Work, pp. 55-69

[5] Time, which could otherwise be spent in more productive problem-solving.

[6] I’m (barely) techno-fluent enough to be able to take notes on my phone or laptop, but I don’t like the idea of having people wondering whether I’m listening to them or shopping on Amazon.

[7] Unfortunately, this office, along with all of Caterpillar’s operations in Russia, had to be closed in response to the conflict caused by Russia’s 2022ninvasion of Ukraine.

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