111: Avoid These Common Communication Mistakes with Alisa Cohn

Hello and welcome to episode 111 of the Modern Manager. I'm your host, Mamie Canfor Stewart. First, a warm welcome to Harsha S and Rocky T. To the Modern Manager community. I am so excited that you have joined us and I'm already engaging with you on the Slack community and I'm so glad that you're there. If you're listening and you haven't yet become a member, please consider checking it out. Memberships start at only $2 a month and you can stay tuned to the end or check out the show notes for more information. Now, today's guest is Alyssa Cohen. Alyssa is the world's top startup coach. She has worked with clients such as Etsy, Venmo and Foursquare and others that.

You haven't heard of yet, but you will.

She also writes for Inc And Forbes and is an angel investor and Broadway investor. Alyssa and I talk about some things that managers don't realize that they're doing that they could easily adjust and that would have a powerful positive impact on their team. We touch on power dynamics, delegation, meetings, micro and macro management, email using multiple communication tools, remote work, and more. This was a super fun, high energy interview that I think you are going to love. Now here's the conversation.

You're listening to the Modern Manager, a podcast dedicated to helping you be a rockstar boss with a thriving team. Whether you're looking to upgrade your meetings, cultivate your team, or grow as a leader, this podcast is for you. Now, here's your host, Mamie Canver Stewart.

Thank you so much for joining me today, Alyssa. I have to first give a shout out to our mutual friend Dorie Clark, who introduced us and she was actually one of my very first guests. She was episode number eight.

Oh, my God. Amazing.

I know. And now you're going to. This is already now like past 100 episodes. Wow.

Yes. Well, Dori is amazing. She's an incredible connector and it was really wonderful to meet you when we did. So I'm excited to be here.

Yeah, I had so much fun talking with you at the dinner that you hosted. And so of course I was like, I have to now bring you on the show because I need to talk to you more.

I love it. Very good. Me too.

All right, so question number one. You're an executive coach, so you talk with a lot of people about their problems and a lot of people who are managing people and their management problems. So what are some of the problems that you hear the most that have relatively simple fixes or, you know, there are a couple things that you can do that will just really make a big difference on those.

Yes, yes, yes. Great question. So a couple of things come to mind, and they're not. They're really related to managers at all across the board. So what? A manager often doesn't realize, whether it's a CEO that I often coach or a senior manager or a junior manager, they don't recognize that they're coming with a certain role, like, as in, I'm the boss. Like, they don't see themselves as the boss. They just see themselves as like them. And so they don't realize that their suggestions are orders to their direct reports. They don't realize that they're coming across and that they show up as like, do this or do that, or there's like, high stakes when it relates to them because they're just not relating to themselves. They're just relating to themselves as them, not as, like, the figurehead or the boss. That's one very common challenge.

And that is so important because, like, I think about teams where the manager will say something or the boss will give it an idea or kind of make an authentic commentary, and then the team goes and executes and they wait a ton of time.

Totally. And they brought up all this time, and it's like, it wasn't just like, oh, I don't remember saying that. Right. So there's that. But also, they fill people kind of with fear, even without meaning to, like, why did you do this? It's like, actually a very simple question, like, just asking out of curiosity, how come you guys did that? But what they hear is, why did you do this? Unless you're very careful with your tone and very clear about kind of your standing. I once had one of the executives I coach stand up on a table so that he could see how he shows up to his people, like, with a bullhorn on the table, kind of talking, like, loudly down to them. You know, he doesn't mean to come across that way, but that's a visual of how he shows up to them.

So how do you not do that? Like, how do you recognize and how do you show up in a way and talk in a way that doesn't create that fear or doesn't kind of send people down some path that you didn't intend?

Yeah. So first of all, you've got to build psychological safety with your team. And, you know, the more I become a coach and the more I recognize, you know, the experience, the workplaces, I just recognize how important psychological safety is. You have to build rapport with people, you have to showcase yourself as not a punisher. You have to showcase yourself as an obstacle remover, as an ally, as someone that they can talk through their problems with and also not going to, like, fire them or snap at them or punish them for making a mistake. So, like, setting up the context of psychological safety in the team is essential. And then I would also say making sure that your tone is conveying what you're trying to convey. So some people have a very direct style or maybe in very authoritarian tone. And sometimes when you're the leader, you actually need to make sure that you're softening your tone. You're making sure you're using more words so you don't come across as, like, very direct, but more like. I was thinking that I was wondering if you had thought more about these kinds of ideas. You know, I'm sort of exaggerating here, but the idea is elongate your sentences and elongate what you're trying to say to give it room to sort of sink in and put words in that shift your tone.

Oh, I love that. I'm already now getting ideas for how I can say things differently because, you know, I feel like my problem is more that I'm very high energy when I talk with people, and so I get excited about everything, and I don't want them to assume that my excitement means.

Yes, right, right, exactly. And I think also for everybody, for all managers, it's very helpful to be clear. So sometimes in our heads, we know it's a suggestion or we know we're just getting excited. That's a great idea. Doesn't mean you should go do it, but it's a great idea. Right. And so it's very helpful as a manager to be explicit in what we just think we just decided and who's going to go do what by when. And also if we're just brainstorming, to be clear, we're just brainstorming. I'm not really sure what you should do. In fact, I think I might want to have another conversation after we both digest what we talked about here today. Making those cues and clues explicit and signaling what you're hoping for also resolves miscommunication and misalignment.

I love it. Okay, what's another big one?

Okay, good. I'm so glad you asked. Delegation. Everybody's confused about delegation, right? So there's, like, so many different ways to get confused. So some of my CEOs especially, but even, you know, as a senior manager and definitely A junior manager will try to delegate to people, as in here, go do this. The person they delegated to can't like, doesn't do it, doesn't do a good job for whatever reason. And then the manager will come back to me and say, oh, see, I tried to delegate, it didn't work. Right. They couldn't do it. So it's like breaking down what's really going on around here. Right? Like first of all, did you think about the person's skill and did you think about the person's experience and also the willingness to do that? So we call that skill and will. What kind of skill and will do they have to do it? And then also did you think about the task itself? Do they need a lot of instruction? Because maybe they're more junior or they're inexperienced in this particular thing. Did you break it down for them in a way that will help them really understand what has to be done? Did you also agree on what done looks like? Did you agree on a deadline? Was there a mid course check in to see how it was going? Those are all really great tools to use in delegation and people don't do them naturally.

I completely agree with that, which is why actually the first online course that I launched was on delegation. Because of that thing.

Yes. Right, so you understand, right? Exactly.

It's not rocket science, but there are just a few things that you just have to sit down and think about before you hand off work. And if you ask yourself those questions about is this the right person for this, do they have the right skill, do they have the will, what do they need to know, how am I setting up the timeline, all of those things. If you just ask yourself those things beforehand, you can eliminate a ton of hassle.

A ton of hassle. And what people will say to me, what managers will say to me as well, I'm not a micromanager. And my thing back to managers all the time is it's not about you, it is about the individual and it's about adapting and tuning your style to what the individual needs to help that person be successful. And when you're thinking of yourself as not a micromanager or I'm a hands on manager, I think what happens then is that you sort of decide you have this one style and that's the way you operate, but you're not kind of looking at what's going to work for the other person. And then to your point about breaking things down, I sometimes think the manager hasn't gone to the trouble breaking things down. Because they don't know how to do that. First, they aren't used to that. But second of all, sometimes it's actually complicated. Like I'm not actually sure what done looks like either. Yeah, well, now that we're pressing into that, how would you think your reporter, your employee would know what done looks like if you haven't really gotten a clear idea of what done looks like?

So true. And I like, I want to tell everybody to do that even before you start your work, right? Before you start a project where you should be clear with yourself, even if you're not delegating to somebody else, but you're just delegating it to yourself, you should be clear with done so that you don't overdo something or underdo it.

Or underdo it. Exactly. Then the other topics around delegation to me that are just fascinating are that, for example, somebody will delegate a little task where you've got a multi stage project and you'll sort of go do this. No context, no understanding of how it fits in. Right? No even understanding of like, I'm going to break off, here's the big project, I'm going to break off a piece of work. Can you do this? Let's have a discussion about what of this kind of project you want to do. It's just go do this, come back to me, go do this, come back to me. Which is actually, that's like the notion of like when you don't like a micromanager, it just feels like it's tasky and it's very like sort of directive. It's very nitpicky. And you don't, as the employee, you're not developing anything, you're just kind of being an order taker and like a gopher and go get this and go get that. And it doesn't kind of fit into a cohesive hole when you do it that way.

Oh, I completely agree. What about when, you know, like I hear more senior managers say, you know, like, well, it's important to give people autonomy or just that, you know, the best managers know how to give people autonomy. Or I want a manager who will give me autonomy. Like, how do you define like healthy autonomy? Or what's kind of the balance between being a good delegator and giving people autonomy and not micromanaging, Right?

Oh, that's such a good question. And in fact you're asking me this question and actually it's the manager and the employees that should be having this exact conversation. Like, what does that mean autonomy? And what does that Mean sort of the notion of being hands on. And I think it's first of all to kind of really have open discussions. That's back to psychological safety. When you have an open discussion and transparent discussion about my style and your style, what you're good at, what I'm good at, what I need help in those kinds of things, that already sets up a context for knowing each other better. And again, having the psychological safety. Also, you have to look at your employee and really figure out how junior, how senior, how experienced, how inexperienced is this person. And then do your best to calibrate how much direction does this person need? And then that's how you learn. You sort of learn by doing. Because when you realize, whoa, this person went way far afield and I didn't realize it, I have to have more oversight here. Maybe not even more control, but more oversight. I want to be kept in the loop more regularly. And then you can have that conversation or if the thing didn't move at all, what happened. Very often people are confused and are afraid to bring it to your attention. Confused, don't know what to do, so they don't make any progress. And so then when you come to check in a week or two later, it's like, oh, I should have had more oversight here, you know, in a different kind of way. So I think you want to constantly be trying to assess, how is my employee going to be able to do with this particular project, this particular task, and then study the results, actually study the results, and then have conversations with that person about what went well and what didn't go well. And by the way, it could also be autonomy. Talking about autonomy. It could also be the person picks it up, runs with it, does a fantastic job, a flawless job, brings it back to you early. You didn't even know it was happening. It's happened all around you. That's fantastic. Is that person possibly ready for more? That is what an autonomous person wants to show you, that they're ready for more or that they can handle things for you without any kind of check in. Those are the clues to look for when it comes to, like the difference between autonomy and more hands on.

Oh, so beautifully said. Do you have another one?

Oh, my goodness. In terms of. Well, I will tell you this. It goes back to kind of the first one in terms of your perspective. You have these voices in your head and you think you're clear this about communication. You as a manager, your voice is in your head. You think you said to other people, you think you're being Clear. And what happens is a strange sort of alchemy of lack of clarity. So I've been in meetings many times where the leader, the CEO or the senior manager or whatever it is, or even just the leader of the meeting is running the meeting. It's like six or eight people in the room. And at the very end of the meeting we're about to go, I'm the one that says, okay, great, so what did we decide here? And three different people in that meeting of eight have three different versions of what we just decided on. Right. And so to me it's like, that's interesting. The manager really has to help people create clarity and promote dialogue and communication amongst their people. But also they need to recognize that their communication needs to be frequent, explicit, in different kind of environments, in large groups, in small groups, in one on one, in writing, on videos. And so it's like a manager doesn't realize how much they have to over communicate before they've really gotten their point across.

Yeah, and I totally see what you're talking about in meetings. And it's one of the things that I always recommend to my clients, which is at the end of the meeting, state the actual decision and write it down. Because that's when you find out like, wait a second, I thought we had.

Said this about the decision.

It's so easy to have the like, okay, we've decided, so let's go. And you're like, wait, what was the actual decision?

Or yeah, and then following on from that, it's also about execution. So we've decided this. Okay, great, goodbye. And then it's like, well, hang on, who is going to do what by when? You know, Mamie, I think we had this conversation when we were at dinner that night. It's just like, this is geeky, the geeking out of meeting.

Right? Like yes.

Right. Like yes, the secret to meeting. But what did we decide here and who is going to do what by when? And it's incredible to me that that's not tied up at the end of a meeting or at the end of a discussion. Then things don't happen. And you're wondering why? Because we decided.

Right.

But there was so many things that happened underneath that decision that didn't kind of get knit up. And so things do not move forward.

Yeah. And to your point about broader communications.

Right.

It's challenging. And I imagine that there are a whole lot of teams who are using a chat tool now who maybe haven't historically because they're now all working remotely. And so the Way that you communicate on chat is different than the way that you communicate by email or in person or on the phone. And being clear and like the lack of tone that sometimes comes across or the ability to misinterpret or misunderstand even, you know, those short messages is really, can be really problematic.

Yes. There's no question. It's really thinking about what you just said is so accurate. Like how do you communicate on each mode, each way, but also what is good for what. So when do I use email, when do I use text, when do I pick up the phone, when do I use Slack? Right. There's sort of all these different ways to get that right or wrong. And then to your point, right now we're all working remotely and so now there's like an extra heavy burden about how do I sort of take the emotional temperature of the room when we're all showing up on video? It's a very different experience now.

Yeah. Are there any kind of pro tips that you have for which communication methods are best for what kinds of engagements?

Yeah. So when you want the notion of asynchronous communication, so you're trying to engage a lot of people, that's great. With email or with Slack. Although I think Slack has this expectation of having a quicker response. But with email it's like, I want to inform you of something or I need an answer over a certain period of time. It doesn't have to be immediate. And then also you can, of course, you know, the notion of storing attachments works okay on email too. Text is like something like, hey, it's really quick, I need to know right now. Or it's sort of casual quick question, I'm working on something right now. Do you know? And so it's more the rhythm of like literally a chat experience of a chat. And then I think Slack, you know, I'm less familiar with Slack. I know that most of my clients have kind of moved away from email and into Slack. And I know that there are places you can store conversational threads on Slack. So we can be very organized in that way. But I also think that it's very helpful to decide on where are you going to store documents, where is going to be the kind of center of truth, the source of truth for this particular project. And Slack is not always so great with that.

Yeah, I fully agree. And I am a huge fan of Slack. And now Microsoft Teams as I've been working a lot inside of it and they're great tools, but they are definitely not the end all be all.

So you.

Yeah. You can't just assume that any one particular tool is going to be it and you can just communicate that way. You do need to actually use the arsenal and you need to be clear with your team, as you're saying, about how we're going to use each one and where we're going to store information. And you don't want to make it more complicated for people because they're looking at a million places.

Exactly. And having guidelines set you free. People think it's like, oh, it's so bureaucratic. It's not bureaucratic. Now I know to look for my. Look my slack for this kind of thing and look at my chat for this kind of thing or that's like the appropriate place to put something or to engage with somebody. And I think that it's really important to sort of think about that as a team so that you're not constantly, like you said, searching out everywhere. And then also it reminds me even the notion, so again, now we're all working from home. It's a whole room working remotely. It's a whole different thing. It's also important still to be able to be offline. So I'm still doing my real work, even though obviously in front of my computer all day. I'm in meetings on, you know, on video all day. But I still want to be able to have the time where I can turn off my alerts, not expect to be interrupted and be able to do the sort of. The deeper work.

Are there things that managers should do on that note to help their team members carve out or kind of distinguish between their hours and things that managers or shouldn't do that are sending the wrong signals about work life balance.

Yeah, well, especially again, now that we're sort of working remotely, I think that's even more critical. So what I've been advising all my clients to do is to make sure that every junior person, I mean, basically everybody in the organization, but like, the more, you know, the more junior you are, the more important it is to have a touch base with that person to make sure they have a workspace set up. It's a comfortable workspace that they understand how to structure their time and give them tips on how to structure their time. So an example would be find a routine. Think about what your office hours are going to be like. Just like any regular office situation. Take breaks every 90 minutes or so. Declare an off time. We're not really good at that, even when we're working in the office. So now how much more so working from home. And so it's about just sitting with people and really helping them explicitly look at their schedule, look at their workspace, and look what's going to make them most productive and then make suggestions. Like, it seems to me if you're being interrupted all day, you're not going to have time to get these specific projects done. So how should we carve out the right time for you to make sure you will? Like I know with my clients, I ask them to carve out two or three hours to at least two or three hours per week to just focus on strategic thinking and strategic projects. And everybody needs to have that time, even though the notion of strategic will be different for each person.

Oh, will you say more about what you mean by strategic time?

Yes. Well, look, for all of us, if we just go through our day to day, if we just, if we show up at the, at our desk with no real plan, the plan becomes responding to email and slack and text. And you can spend a whole day doing that. You could spend your entire day just responding to email and maybe doing like one or two proactive things or sending your own email and shooting your own meal asking questions. So you need to get in charge of your own day. This is true for all of us. And managers have to help employees get in charge of their own day. Which means think about, like I would say on a Sunday or a Monday, think about all the things that you're actually working on. Think about what the most, one or two, one or two maybe most important things are. And then schedule the time during your week when you're going to make progress on those things. Because those are the notion of like the Stephen Covey important but not urgent. They don't have deadlines maybe, and people are going to, you know, bug you about all the things that you're supposed to be working on that are also important. There's no question. But if you don't carve out specific time to do your most important work, your most strategic work, it's just not going to happen. Doesn't specifically happen. That's true for everybody. And managers may not know, like, so what is my most important work that is actually really good? Like, I think it's your most important work to sit down and ask yourself the question, what's my most important work? I think that's a starting point of everything. And it may be a functional task, like helping build a service organization for one of my clients, helping roll out or launch this one particular release and software that may very well be your Most important work, it's your job is to coordinate that. But it might also be, I have eight direct reports or five direct reports I need to sit back and think about. Are they all fully enabled? What are the strengths and weaknesses? How do I make them better? Because they're, you know, in case of five, if they're like 10 hands and 10ft and five brains are all launched on something, I don't care how smart you are, it is much better than your two hands, your two feet, and your one brain.

You know, it's so funny that you. You said that because I was listening to one of your podcasts that you were on previous to this when I was kind of prepping for our call, and there was something that you said that just really stood to me, which was something along the lines of, your job as a manager is to help make sure that your team members make progress.

Yes.

And you can't do that. Kind of strategic, like, how am I making progress? If I'm spending my whole day on email, then I'm probably not making progress. And if I'm not taking time to think about what's my most important work and how am I enabling my team members to be most successful, then you're probably not helping them make progress.

Yes, exactly. Also, you're not being a great role model. Like, I think also great managers are great role models in terms of how do I think about my time? Am I doing the most important work? Am I supporting the right people and the right projects? Am I building the right relationships? Am I connecting other people? Am I being an askable manager? Right. All those things are also great things that you need to role model as strategic imperatives so your team sees you doing that.

So I want to switch gears a little bit and ask you about one of the awesome rockstar managers that you had the privilege of working for and what made that person so great?

Oh, I love this question. You know, I have a go to on this, and my first manager out of college, Beth Shaughnessy. Beth, if you're out there, I appreciate you. I showed up as a very shy, sort of just recently graduated, like, just graduated from college kind of person. And I was super shy, and I didn't really understand how to navigate in the workplace. So although I'm smart and proactive, so sure I did a good job. And we came to performance review time, and Beth, who really spent a lot of time and energy with me and appraised me all the time and supported me, she said, alyssa, what I really love about you is you're really smart and you're able to figure out what the problems are. That's fantastic. What I'd like you to work on more is how can you think about what the solution is, not just the problem, also the solution. How can you be more solution oriented? So again, notice how she gave me that feedback. So loving, so praising, so wonderful. And after we were done, I was like, I totally want to do that. I'm inspired to be more solutions oriented. That was a long time ago. I've never forgotten that or heard what.

Great advice and what great advice for every manager to talk to their team members about being solution oriented. I love it.

Yeah.

Yeah.

Awesome. So we are out of time, unfortunately.

Tragedy. Tragedy. So fun.

I know. I want to continue anyways, but so where can people learn more about you and your work?

Oh, good. You should come and see my website, alyssacon.com a l I s a c o h n.com come and say hello and subscribe to my newsletter and also follow me on Twitter, which is lyssacon A L I S a C O.

H N thank you so much. This was so much fun. And like, I just feel like we have, you know, this symbiotic are. I don't know, I don't know how to describe it, but it's just awesome.

Yeah, yeah, I feel the same way. And it was great, great to spend time with you. I really enjoyed it. Thank you for having me.

In honor of this conversation, I am relaunching my online course on delegation. It got rave reviews the first time.

Around and I have made it even.

Better since it was released this past January. So I am super, super, super excited to share this new and improved version with you. To learn more and register for the Modern Manager's Guide to Effective delegation, go to themodernmanager.com courses. Members of the modern manager community get 20% off of this course. And if you are not a member and you want to grab that early bird pricing, that ends July 28th and you can use the code early 10, that's E, A, R, L Y, the numbers 1, 0 and an exclamation point. To become a member, go to themodernmanager.com join and when you become a member, you get that 20% discount plus many more membership perks. All the links are in the show notes and they can be delivered to your inbox when you subscribe to my newsletter, which is at that same website. Themodernmanager.com thanks again for listening. Until next time.

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