Annual Performance Review Role-play


Some of you were blown away by the plenary session that Paul Gaffney, currently Chief Digital Officer for Omni Logistics. Previously, he was the head of software for The Home Depot, CTO of Dick’s Sporting Goods, and CTO and head of supply chain at Kohl’s.

Paul had made the observation that many technology leaders might be doing their subordinates’ jobs instead of their boss’s jobs. So during the breakout, I asked him to do a role-play he did with Jeff Gallimore, where Jeff played his boss, who wasn’t very interested in having Paul do his job.

It was an amazing demonstration of modeling how one starts that conversation, and what to do when there are clearly issues that need to be fixed beforehand.

At GeneCon, Paul and I did another role-play, where I was the boss presenting his annual performance review, and the main advice he got was, “Keep doing what you’re doing.” This is not particularly helpful advice and certainly doesn’t help advance one’s career.

In the role-play, Paul again wonderfully models taking responsibility for getting the feedback he needs even if it might be hard for him to hear, making it possible for his boss to share it, and gets some surprising feedback.


Paul Gaffney

Chief Digital Officer, Omni Logistics


Gene Kim

Author, Researcher & Founder, IT Revolution



So, yeah, I first talked with, uh, Paul Gaffney, uh, former head of software for the Home Depot, uh, former CTO of Dick's Sporting Goods. He was CTO and head of Supply Chain at Kohl's, which is actually when I, uh, finally talked with him in 2020 after years of admiring his work <laugh>. And, uh, one of the, uh, thing that really caught my attention was that the, uh, uh, of where the genesis of software modernization came at Home Depot. And it wasn't the e-Commerce Group, it was, uh, equipment rentals. And so he told that story, uh, some years ago, and I can't, um, uh, overstate just how much I've learned from him over the years and every interaction. So I finally met him last year. He spoke at the last two conferences, and it was always some of my favorites just because of the profundity of his insights and just the amazing advice he has to this community.


Last year, he, no, I'm sorry, two months ago, he's co-presented with Courtney Kissler, where he had made two kind of startling observations. One was the observation that so many experience reports were focused primarily on efficiencies, uh, as demonstrated by the value, uh, uh, readout this morning from, uh, Matt Ring and Team. And his observation was that efficiency is what you can safely delegate <laugh> versus effectiveness, uh, which you can't, uh, right? So, uh, if you wanna be doing your boss's job, efficiency is, uh, not going to be sufficient to get you there. And, uh, that actually gets to the next observation, which is that so many technology leaders may actually be doing their subordinates job, <laugh> doing instead of doing their boss's job. So, um, Paul, uh, I capture that correctly. Maybe could you also introduce yourself? And I'm, so, I'm so great to see you again, and you're muted.


Darn. That auto mute. Great to be here. I I did not receive my Jean Khan, uh, glasses in advance, so I went spectacle <laugh> free today. Um, and, uh, thanks for a reminder of those points that, uh, that Courtney and I tried to drive home on stage in Vegas. Um, I do think it is, uh, super important on a leadership journey to recognize the amount of time on your calendar that's going toward efficiency, making things maybe a little less expensive, maybe a little more reliable versus effectiveness, which is really questioning are we working on the right things? Uh, and if we turn some attention to some more lucrative things, um, would, you know, would we be a more effective company and overall organization? And those, those are the discussions at the big tables. Boards don't generally get presentations about modest improvements in efficiency.


Yeah. And before we kind go into the, uh, to set up the role play, um, there's actually an extension of, uh, the, the breakout session that you did in Vegas. And I re-watched that, uh, yesterday, and I thought it was just, uh, extraordinary. And there was a, a part where, uh, I asked Jeff to role play, uh, being your boss that, uh, is not, uh, so interested in, uh, having you do my job, <laugh>. It was just amazing to see you model, you know, how does one open up that conversation, right? Um, and, uh, uh, allow room, uh, for that. So, um, uh, Paul, you had mentioned that, um, you know, there's another factor at work, which is that sometimes technology leaders sometimes need to work extra hard to get the feedback they need, you know, to actually, you know, achieve their own goals, better advance their careers. Can you tell us more about that thesis? Uh, or do you wanna jump into the role play?


Well, we should definitely talk more about that thesis, but the role play might, might set it up. And I was just kind of excited today that you're gonna give me a performance review in our role play. So


<laugh>, yes, yes, yes. Um, yeah, I'm so excited for this, uh, uh, performance review meeting, Paul, and, uh, um, uh, sorry, it's only 30 minutes and that we started 15 minutes late. So that gives us about, uh, uh, and I have another meeting that's urgent. So we have about, uh, five minutes tops, <laugh>. So, uh, let me pull up the document here. So yeah, I have about three bullets. Um, overall performance reading rating. Um, as you saw in my email, uh, uh, you meet expectations. Uh, your work is really good and I would love to give you a higher score, but, uh, I'm only allowed to give those to the top 10%. And, uh, cannily speaking, you know, uh, you're not there. Uh, key responsibilities, you know, you achieved your project goals, splendidly mostly on time, mostly on budget. Uh, so, uh, the next field here is, uh, evaluate progress and system goals for next year. You know, you mostly do what you commit. So my overall advice is, uh, keep doing what you're doing. So, good job, Paul. And, uh, thank you,


Um, g as always, I mean, I know your time's super valuable and, uh, and we don't have a lot for this, uh, for this performance review. And, and I, I get the sense that, that you, um, feel kind of the same way I feel about the formal process. Like there's some boxes on the sheets and things, but, um, as, as you know, I, um, I believe I do a good job, uh, technically, but I've been wanting to get involved in more things. And, um, if I just keep doing what I'm doing, I don't exactly know how that's gonna happen. So what, what might I do? I mean, I'm, I'm definitely gonna keep doing the good job you just praised me for, um, but you know, what, what can I do to get involved in, in some things that, that might advance my career?


You know, um, Paul, it took me about two hours to fill out your performance review. And, uh, I think my primary advice is just keep doing what you're doing. Um, you know, uh, they say focus on your strengths. And, uh, I would say just, uh, you're going in the right direction, Paul.


Yeah, I, I, I, I really appreciate the support and, and the feedback. And I'm wondering, is there, is there something, um, that you are worried about, like how I might react if you told me something that maybe I don't want to hear? 'cause it, it kind of sounds like there, there might be something holding me back. Um, and, and, you know, I don't know. I, I, I imagine sometimes you give that kind of news to people and they're super defensive, and I wanna make sure, you know, I'm, I'm like not. I just, I'm, I'm really interested in knowing like, what's going on, what do people say about me behind my back,


You know? Um, since I have to leave about five minutes, uh, I really would just like to assure you, you know, just keep doing what you're doing and, uh, you know, I think, uh, we'll have another great year together, Paul.


Yeah, I, I hear you. And, um, I've really enjoyed everything we've been doing, and, and I'm gonna, I'm gonna keep on keeping on, but, but, you know, I have, I have bigger aspirations. Um, and so if there's really nothing more for me here, um, I, I'm gonna keep doing a good job for you, Jean. Um, but I, I gotta start thinking about what, what might be next. Oh,


Oh, you, you're not thinking about leaving?


Oh, no, no, no, no, no. I'm, I'm, I'm thinking about how I might expand my career, and I sure hope the answer isn't that I should be thinking about leaving.


Oh, <laugh>, uh, I mean, uh, thank goodness because, uh, yeah, recruiting is really, really tough. And last thing I wanna be doing is a bunch of, uh, interviews. So, uh, let me, let me share with you something, Paul, uh, uh, you know, I'm not sure if this is useful to you, but, uh, I've actually had a bunch of people tell me on your team, uh, that, uh, they've actually come to me instead of you. And they say that when this project is over, uh, they would really like to leave your team. Uh, in fact, uh, one of 'em said that, uh, they would, uh, quote, never want to work with you again. Uh, don't exactly know what to do with that, uh, Paul, but, you know, maybe that, uh, it would be an area of improvement that, uh, you know, might be very useful. I'll tell you right now, that, you know, uh, having, uh, you need to have people that, uh, can not only get the job done, but you also need to create a team, you know, that is going to continue to do bigger and better things.


Man, it, it, it must be hard to share that, 'cause it's hard to hear it. But I, I actually really appreciate knowing that I, I, that gives me something new to think about and focus on. And, um, and you've got my commitment. I'll, I'll do something with that.


And what would that something look like, Paul, or, or you can end the role play here. Just the, yeah. Whatever best serves the


Learning objective, we, we can end with, you know, I, I don't know, but let me go think about that and, and when we can find another five minutes. Let's, um, <laugh>, that was a joke.


<laugh>, fantastic. I'll let you take it over from here, and maybe we can reflect upon like what was actually happening here. <laugh> and is uncommon.


Yeah. And, and, and we, we, we teed this up. Um, and I, I suspect that most people in the audience would, would notice some similarities to the performance appraisal process that they go through. Um, it is often very perfunctory. Uh, it is, um, uh, sometimes challenging to get a genuine discussion about improvement. Um, and it's because of, uh, a lot of things that we've talked about, uh, over the past year or so. One is, in many cases, the boss's reaction to a job not getting done well isn't to attempt to get their subordinate to perform better. It's to step in themselves, uh, and, and do the job. Uh, and then that leads to, all right, job got done. So performance improvement is, you know, meets expectations. Um, and then the second thing is, I, I, this certainly happened to me. Um, Jean, I think, I think it happened to you.


I suspect it happens to a lot. Um, early career technology folks often accelerate their career because of their technical competence. Um, and, and some, but not all, but some certainly, um, leverage over-leverage that technical competence and, um, don't develop the personal connections toolkit that, um, that needs to complement, uh, competence. You know, success is a balance between competence and connections. Um, and sometimes people are in assignments where they view, and their manager doesn't tell them anything differently. They view their contribution largely as one of competence. I had someone working for me once I had to deliver similar performance feedback. Like basically I said to this person, nobody likes you. And this person said, I understand that no one's ever liked me. That's why I was a math major in college, right? I didn't want teachers to be able to take out their dislike on, you know, um, gray answers and math.


The answers were right or wrong is the perfect illustration of over rotation to competence. Um, and then I think people find it, it's a lot easier to give competence feedback. It's a lot easier to say, you know, you introduced too many bugs into production. Here are some tangible things to do that's measurable these discussions about, you know, people have a bad emotional reaction to you. There are icky discussions and, and people don't like to have 'em. And, and they're much more challenging to action than, um, like, you know, how do you put that in your performance goals? Please increase the percentage of people who like you by 20%, right? There isn't even necessarily a baseline, but these are often the issues.


Then I if, uh, just to reflect, I mean, I thought there were two kind of startling things that you did. And by the way, uh, this is just, uh, one of a dozen that you'll see in the role play, um, of the breakout session that you did in Vegas, uh, which we'll find a way to get published. One is, um, uh, a way to overcome the, uh, reticence of the manager to actually talk about these uncomfortable questions was, uh, you know, to reiterate that, you know, you, you have these career goals, right? And that two is, um, um, you know, you're continuing, uh, your continual desire to try to get that difficult feedback right, that you needed. Um, and by the way, that was actually based on my own performance review, <laugh>, that was actually shared that no one likes you was actually my boss at Trip or the CEO remarkable leader, Jim Johnson. Anyway, uh, could you, uh, maybe concretized that those are two sort of techniques you're using. Oh. So what is more unpleasant than having a difficult conversation, having to replace you <laugh> and all the hiring, uh, and the work that you're gonna create for me? Can you validate that those were kind of the, kind of some of the techniques you were modeling?


Yes, yes. Um, those who saw, um, uh, the talk I did with Courtney, um, saw that one of the key takeaways was gracious perseverance. Um, and, and in this, in the realm that we're in today, which is advocating for your own career, um, you know, I, I encourage everyone, you have to be your own career advocate. You're the really, the only one that you can rely on. Um, but you have to find a way to, to do that, uh, graciously. So you have to persevere. You have to be your advocate, you have to do that continuously. Um, but you have to be gracious about it and recognize when you're in a potentially uncomfortable, uh, conversation where you are gonna be uncomfortable, but it's the other party's discomfort that probably requires a little bit more attention in the moment. Um, so I, I tried to role model that, uh, in this, and, but there is, there is that line, right?


Um, I, I threatened my boss, right? I, I, I hope I did it in a very cautious way and avoided the line of, you know, if you don't give me opportunities, I'm leaving. Um, and, and that's always a little bit risky. Um, so, but, but in advocating for yourself, sometimes you have to put the trade off in front of the other party in a way <laugh> gets them to recognize, oh, there is a trade off here. I can't just keep stonewalling. And, and we've all worked for a lot of managers who would rather stonewall than have the hard discussion.


Yeah. Um, and maybe just to, uh, so, so I've never, uh, told this, but, uh, yeah, as someone who, uh, was very conflict averse, uh, there was a certain conversation I couldn't have with my boss at Tripwire and, uh, stoly that the person I learned this from was, uh, uh, our VP of sales, uh, who passed away Bob Dunn. And I would go to him, it was like, here's all the difficult conversation I want to have, uh, what should I say? And he would tell me the lines, but I didn't know <laugh>, what we would say next. I actually had him say, alright, he gave me all the objections, and then he also gave me how to negate the objections. <laugh>. Yeah, yeah. Uh, just to learn what it looks like to have a difficult conversation. It's something I'm just so enormously grateful for <laugh>. Yes, yes. Um, what other advice would you give, uh, uh, you know, to technology leaders, uh, who are looking at ways, you know, if they feel like, uh, they've hit some sort of ceiling or not able to make meaningful advances in their own objectives and goals?


I, you know, I, I think this, um, this next piece of advice will, will compliment, um, the discussion that you're gonna have with, uh, with Admiral Richardson about, um, about connections. Uh, do a connections map, um, you know, have, um, m much like, you know, if you've, you've grown up on the technology side of, um, of enterprise technology and you've been, um, you've drawn, uh, technology architecture charts, you know, how the components of a system connect, know how the components of your network connect and, um, you know, do the, do the empirical work of, Hey, here are the 10 most significant people in my professional life, and here's the temperature of my relationship with them. Um, and, and that can include non-existent, like I have, I do nothing but transactions with this person. Um, and if you have relationships that are purely transactional, uh, you should find a way to deepen those connections outside of the context of actually just doing thing, doing tasks together.


Um, and if you have, you know, if you have, um, warm relationships and good connections on that chart, ask those folks to help you with the connections that aren't so warm, um, or, you know, or that aren't, um, uh, aren't, or that are purely transactional. Don't, don't expect to get the whole map, um, rosy, uh, you know, we, we are all people. Some, some people just are, you know, uh, a connection between any two people requires both people to a certain extent. And you can only work on you, but, but work on, you do the, do the map.


And by the way, for a cold relationship, what does a warmer relationship even look like? Where do you start? What is the, uh, what is the kind of the series of steps to get from here to there? What does that look like?


Well, you know, Jean, you and I have known each other now for I think, maybe about 18 months. Um, and we, um, I, I think if, if anyone could see the way that you and I have built a relationship, they would see a nice balance between us getting to know each other as people and us doing work together. Um, and we don't have any formal, uh, professional relationship, but, um, we, we wouldn't have a personal relationship if it weren't for some shared professional content. But I, I mean, I would like to believe we haven't done a Gene Paul relationship review, but, um, <laugh>, but I'd like to believe the performance review would be, would be pretty good. Um, and so I think that that's one key element that, that, um, warm relationships are ones where there is a good balance between paying attention to the other person as a person and doing some work together with that person.


That's, to me, what a, what a warm personal relationship looks like. Um, and I think the warmest personal relationships are ones where conflict would not be icky, um, where a disagreement, um, could, um, could be discussed. Pat Lencioni talks in, in a variety of his models. This, this kind of shows up in, in many of them in many different ways. But it shows up in five dysfunctions of a team, which I think is the most broadly known one as a preference for harmony over conflict, and sometimes this preference for harmony over conflict, which, which is a problem, by the way, you should actually prefer conflict, right, right, right. To to, to false harmony. But a preference for harmony over conflict are people who overinvest in trying to make everything conflict free. Um, and that actually makes it much harder to have non-emotional, um, conflict, which often happens if you're doing serious work. Um, there will be different points of view and they need to get reconciled.


Yeah. If I can sort of, uh, sort of <inaudible> some words to what you said is, uh, uh, maybe just to fill out the word cloud, you know, a mutually respectful relationship, a sense of a common journey, common goals, <laugh>, uh, helping one another, right? I think those are all things that have contributed <laugh>, you know, to, uh, what makes for just a fantastic, uh, working relationship. So even though we have, uh, as you mentioned, there's no org chart <laugh>, that's as, uh, uh, that would actually describe that. But, uh, it is been so fun to be a fellow traveler with you, Paul. And, uh, I just wanna reiterate, uh, just how much I appreciate, uh, you teaching this community, and I just, uh, uh, there's just no, this further reinforces, you know, that there's so much in experience and, uh, advice that you have that is of such incredible value. Um, we did something at the end of the role play in, in Vegas that I'd love to reiterate this again, is that, uh, if you have any interest in, uh, talking with Paul, um, and contacting Paul, uh, uh, what did you say? Uh, was it DM Jeff and we'll, we will get, uh, we'll figure out some way for you to be able to, uh, connect with Paul. Is that


The right guidance? Yeah, I'm follow to follow up on the session that we had in Vegas, and this reminder, uh, Jeff got me the, uh, the list of folks who submitted their emails from Vegas. I've had that for a couple weeks now with, with full intentions of doing something with that. Uh, and, and I will, um, and anyone who did not, um, either wasn't in that or, or was in that but didn't send their email in or is on this call and wants to be on, I'm, I'm going to do something with regular frequency, um, with that group. Um, so you can send me your email directly. I'm, um, and, uh, I promise before 2023 is over, uh, we'll at least get the first email out to that group.


Super, super fantastic. And again, uh, what, uh, if you have any interest, uh, in what Paul's been talking about, I would strongly encourage you, <laugh>. I think he would be an idiot not to take, uh, Paul up on his offer. Uh, Paul, thank you so much, and I'm looking forward to a whole bunch of other cool stuff to work on and more adventures ahead in 2024.


Thanks, Jean. There's, I'm, I'm reminded that there's, um, some very large number of end of year celebrations that, um, some of 'em have already happened. I think Diwali kicked off the celebration season this year, and, and, uh, Hanukkah starts, I think later this week. So whichever one of the several dozen, um, or ones, because it's nice to be pluralistic. Uh, I hope you, and, and everyone here on Jean Con, um, has a wonderful set of end of year celebrations. I'm personally looking forward to Festivus, um, but I will, uh, dip my toe in the waters of, of several other celebrations as well.


Right on. Uh, hey, thank you so much, Paul. Um, and catch you soon.


Thanks, gene. Bye. <silence>.