Giving 1:1 feedback remotely w/ Jeff Epstein, CEO @

Giving 1:1 feedback to your team remotely requires intentionality. In what format you're giving it, how often, and based on the type. Positive or constructive. We dig into the how/when/why/what of giving remote feedback to direct reports.



4/25/202123 min read

Here's the recap...In today's episode, we chatted with Jeff Epstein, CEO & Co-founder @ We spoke about how to provide 1:1 feedback to your team; both positive & negative. We spoke about what formats to use (text, video, audio). How often to provide it (immediately, review periods, or something in between). In addition, to some other great feedback...

Related References

Jeff Epstein Linkedin

Jeff Epstein Twitter

Before giving feedback be sure to create an environment to receive it

Before you start dishing out feedback as a leader, you need to create a safe and open environment to receive it. Feedback is 360 degrees. One critical way to do so it not shutting down incoming feedback or getting defensive. This will immediately end any feedback coming from your direct reports. Next, is to thank the person for sharing the feedback with you confirming you'd like to review and go over their feedback.

I'm also a big believer as a long time project manager to track and share updates on that feedback. A couple easy ways to do this is by using a Trello card of the feedback action item or by including it in future 1:1 conversations as an active/closed action item. Your team need to know you've received it, you're going to do something with it, and what you've done with it.

How often should you provide 1:1 feedback

Across the board, we all agreed you should be providing positive feedback to your team often. I personally try never going more than 10 days without giving some positive feedback to everyone that reports into me. By giving frequent positive feedback you make the recipient happier (obviously), but more open to receiving constructive feedback. Since you're always complimenting them, they can better accept the opportunities to improve (which they may then be complimented about later). In addition, don't wait for major actions or milestones to provide positive feedback. Your team shouldn't need to close a major deal or push a huge feature to get a 👏.

As for negative feedback there was a bit of opposing theories here. On one end, giving the constructive feedback as it happens. Ensuring it's fresh in mind. While this is definitely the answer for a more severe item, there was a bit of an opposing view. Instead, packaging smaller items that don't need to be addressed immediately. Either sharing them via quarterly review or after a number of weeks and a number of smaller items. This way preventing your team from dreading seeing your name pop up in a Slack notification.

How should you give feedback.

We all agreed a mix of public and private feedback for positive feedback is great. The 1:1s, and shout outs in company/team meetings, or a team Slack channel, or perhaps giving them a Bonusly bonus (or similar). This allows the rest of the team to jump on the bandwagon with additional encouragement. Positive feedback can be given via text, video call, rewards tool, or other.

Constructive feedback must only be done via synchronous video call. It's simply too easy for the written feedback to be misinterpreted. So please don't do this.

What to do when constructive feedback isn't received well

Two great things you can do here. The first is ask for context into why the person did what they did. In many cases, it's previous baggage. From a previous company, from a previous boss that told them to do it this way, or perhaps an outdated policy. Understanding their thoughts and mindset are invaluable to you as a leader.

Help them understand the why and the bigger picture. How the action they did impacts the company's bigger picture. For example, a developer pushed code without testing it first. Resulting in major downtime. There may be some good reasons or history that led to this action. But you can explain how not the down time from no testing code, caused a client to lose a sale or some similar impact. This extra and deeper insight helps your team see the bigger picture, and how their small action really impacts the greater team.

Scott: [00:00:00] Hey everyone. Thank you for tuning into today's episode of Leading from Afar. I am Scott Markovits here with my cohost Tevi Hirschhorn. Tevi, how are we today?

Tevi: [00:00:08] Doing good, Scott, how are you?

Scott: [00:00:11] I'm doing well, thank you. So today we're going to be talking about one of my favorite leadership topics, giving one-on-one feedback. And we're very happy to be joined today by Jeff Epstein. He's founded a few companies prior to Jeff, usually the way we start off is by telling us a little bit more about yourself and how you came to create

Jeff: [00:00:31] Yeah, thanks for having me. So I have a pretty unique background. Originally went to law school in Chicago after undergrad and decided pretty quickly I didn't want to practice law and started a company in the affiliate marketing space. Actually based on online poker, which was pretty popular in the mid two thousands.

I ended up selling that company. Pretty, fortunately, paid off my loans, which gave me the freedom to start a couple of different companies. Ultimately the one that took footing was a company called the Ambassador. Which I ran for almost 10 years and recently sold in 2018.

How this leads to Onboard is during Ambassador, one of the big challenges for us was to mitigate churn. And really work with enterprise companies and get them to use our technology. Obviously, we had lots of great customers, but if they didn't use this, if they didn't integrate the technology and the integrated software, then their team wouldn't use it.

Thankfully Will Stevenson who's my co-founder at Onboard came up with a great solution. Really cobbling together several tools to create a pretty great onboarding experience for our customers. And we said, there has to be something better than this that we could use. There really, unfortunately, wasn't.

As we departed Ambassador and thought about what we wanted to do next we said, "we have to try to solve this onboarding challenge." So we built, which is to help companies streamline the onboarding process for the companies using their technology.

Tevi: [00:01:52] Very cool. Thanks for sharing. How might be helpful for remote teams specifically?

Jeff: [00:01:59] Sure. One of the biggest challenges that we found with onboarding is many times when you're implementing software, lots of people need to do lots of things. And sometimes they're all in the same office, but oftentimes they're all over the place in different time zones, potentially in different teams.

Sometimes people don't even know each other. They just know a certain department may have to handle something. Whether it's compliance, engineering, or design. What Onboard does is creates a collaborative environment for people to manage the tasks and who needs to do what and when. Along with all the details.

So one big part of onboarding is really just wrangling all the stakeholders together so they can get the job done quickly. Instead of it going to one person, everybody has visibility. Which is a huge part of onboarding. So especially in a remote environment, anyone can access it pretty easily.

Scott: [00:02:46] Very cool. So one of the questions that I have before we actually dive into giving one-on-one feedback, it's creating and fostering an environment for getting feedback from your team. So I'd love to hear what you in your experience at Onboard and previously do to foster that environment. Create that comfort for people on the team, to be able to share honest and transparent feedback with you.

Jeff: [00:03:08] It's a great question. And it's something I certainly haven't mastered or even, maybe not even good at, to be honest. I try to learn to be better. It's something that you have to learn through experience. Hopefully, you can read books or read or hear podcasts. But being in the moment with people it's always a little bit challenging to act the way you want to act or the way that maybe you should act. So I think the thing that I've learned most in this is, through the course of managing folks and running teams is, I think being vulnerable and being honest and transparent is really important.

More importantly, is not shutting down feedback or being defensive. Everyone says we welcome feedback. We'd love feedback. I think what's more important is that how you act when you receive that feedback? It's really easy and I think human nature to immediately become defensive and explain why that may not be true.

Most often I found that the best thing to say is thanks. I appreciate that, and I really want to think through that and explain why that happened and it shouldn't have happened. I think those scenarios and not just in business, but in life, tend to create a much better dialogue and ultimately hopefully better relationship between two people.

Scott: [00:04:14] Quick follow-up question to that. Do you do anything specific to show the people on your team that you're following through? So creating, I don't know, it could be a Trello card or something in your one-on-ones and saying, okay, last week you gave me this feedback. I'm taking this into account. Giving some kind of regular feedback on that or that transparent view of, "I've understood the feedback, and here's what I'm doing to try to implement changes or give you access to that."

Jeff: [00:04:40] Yes. And I'm not as organized to have necessarily a Trello card, although I think that's a great idea. I do believe from a leadership perspective, the first part is accepting the feedback in a sort of graceful way and not being defensive. But I think you bring up a great point, Scott. The main part is actually the follow-through and showing that you're taking it to heart. And that you're actually trying to do better or respond to whatever the feedback is. And say, "I thought about it, we're taking these steps."

Oftentimes we're working behind the scenes to fix things or to change things that people gave us feedback on, but we've rarely made those announcements. . And for many reasons, but we thought, why set the expectation or set a timeline when we don't know if some of these things are out of our control, et cetera.

We found that people would assume that we didn't care about it, or we ignored it. So even though, maybe at the end, like months later, you fix it or you make it better up, until that time when you make it better, they're still mad or believe that you didn't do what you said you were going to do. Or you didn't take the feedback properly. Even if you make it right, for example, you still create not the best scenario where people may be, disheartened by the way that it was handled because there's a lack of transparency.

So following up pretty quickly can make that a lot better. Say, "Hey, here's our plan. I can't tell you a date, but we're starting to work on it now." Over time I learned that was important. And maybe it's obvious, but for me it wasn't. That really changed the way that we worked with our team and talk to folks. I try to make it a point, at least once a year, to have an hour lunch or coffee with each person on the team. And just try to bring that stuff out. That was one thing that I learned that by doing that, you can gain some trust but also take the hard feedback which you need to hear.

Tevi: [00:06:25] You touched on something, you mentioned how you have to accept it gracefully. I think that's super important that if someone's going to be making themselves vulnerable they have to know that it's not just safe for them, but that it's something that you appreciate. It's like a gift that they're giving you. They're telling you, you could do something better. I think that's super important.

And you mentioned follow-up. I know in product management, what I do when there are feature requests, bugs, issues that are opportunities to address.

So I'll often let the person know. "Hey, thank you so much for letting us know about this. I'm going to do X, Y, Z." Which is committing to some short-term something. Which may not be an actual execution of that plan. But if you want to follow up with me later to find out the progress, feel free.

It's letting them know I'm listening and that I'm doing something about it. But then it's up to them if they want to actually learn more, they can follow up.

Jeff: [00:07:10] That's a great strategy. I'm definitely going to borrow that one from you. That's awesome.

Tevi: [00:07:16] So what do you think is the best format to provide positive feedback? You as a leader, when you deal with your direct reports or your team, how do you provide positive feedback and reinforcement?

Jeff: [00:07:27] I think positive feedback, you have a lot more leeway in my opinion. I think positive feedback oftentimes can be public. And should it be public, to the team the organization potentially? I think face-to-face, or via video is also helpful. But I think with positive feedback, it's important to give it more often, certainly than constructive or negative feedback. I've found that just mixing up all the various channels. Via Slack in the main channel specifically calling out people and saying great job or excellent.

I think those things go far. Everyone loves recognition, right? As leaders, the higher up you are the less potential recognition you're going to get. And that shouldn't be a reason why you don't give it to other people. That's part of the job and I think it's important to recognize folks are doing well and working hard and getting the things accomplished that they set out to. So I think all channels work, but I do think a public acknowledgment is helpful.

We used to do stand-ups every week at Ambassador, and we would acknowledge several people that embodied the values that we had. And so they would get recognized in front of the whole team. So we did that on a weekly basis, but we also did it, all the time via Slack and obviously one-on-ones and things like that.

Scott: [00:08:41] Cool. Before I dive into my question, I'm going to take Tevi the question you just asked and point it back at you. Maybe sharing your strategies of giving positive feedback.

Tevi: [00:08:49] Yeah sure. So a lot of what Jeff said. I like to do it immediately. I think that's important. Then I also try to log things so that if there's a one-on-one a week later or a quarterly review, then I've got that positive impact. Whatever it was that happened, I have a list of all that. I think it's important to take note of everything that's going on so that it's not just up to you to remember it. Maybe I'm just getting old and sleep-deprived. So I forget things, but I think it's important to keep a log of it as well. And then the feedback I think should be both public and private.

I don't think you should choose one. Public is great, but it's important that people know that on a one-to-one basis you really genuinely saw what they did or you appreciate what they did. And they should hear that on a one-on-one basis. It's received differently than in public. I think they're both important. What do you think?

Scott: [00:09:35] I agree completely. Maybe the two points I'd add in. I have always used the policy of never going more than maybe 10 days, max, without giving positive feedback. Always trying to make sure that you are giving a significant amount of more positive feedback than constructive. The second piece that I had of course now I think is slipping from my memory.

It came back to me now thankfully. Is in many cases, I've seen leaders look for specific milestones to give positive feedback. So somebody closed a big deal or somebody launched a new feature. Especially with the 10-day approach of it doesn't necessarily need to be a big milestone, but it could just be consistent good behavior. This person continues to do a great job in X, Y, or Z every month and calling that out. If they don't have specific closed deals or any major achievements in that timeframe, at least finding something again that you can call out. Thank you for your continued great work or thank you for being a great representative for the clients or things like that.

I think that's the two additional points that I put in there. To the next question, I'll address it to both of you. On the other end, constructive feedback. When should you provide that one-on-one constructive feedback?

Be it the time exactly that happens. Should it be the next one-on-one meeting? During quarterly yearly, whatever it is, time reviews? Or is there a certain right time to be able to give that constructive feedback? And again, I'll open to both of you guys.

Jeff: [00:10:55] So I think it's very situational. Ultimately the sooner the feedback on something that's not great, the better. But I do think ideally you're not embarrassing the person. So yelling across them to meet with you is not appropriate.

You have to be careful about really calling them out. For the most part, I think it certainly has to be private. That is one thing that I think is pretty important is to not embarrass people. Obviously, understand for them, 99.9% of the time, these are not intentional actions, right? They're usually just things that can be improved on. I do think these are situations where are more apt to keep a list. So if they're minor and they're not even worth creating a big fuss about, just keep them in mind for the next review. Which we do quarterly.

But I do think in the event where it's something that needs to be addressed. That it should be done quickly and privately and ideally face-to-face. Obviously, it's delivered much more impactfully there. It's not easy to do, but what's worked best for me.

Tevi: [00:11:57] So I guess I'll go. I think first of all, for remote, you have to be really careful because it's very easy for a person to misread your tone in let's say text on Slack or email. So you have to be really careful how you deliver that feedback. Generally, I would agree with one-to-one, video is important, especially in remote.

But I think that you have to ask yourself some questions about what it is that's happening and what the feedback needs to be. Is it time-sensitive? Is it something that has to be said now? I have had to say things sometimes in a meeting where technically it's a negative, but if you have to make someone stop doing something that's hurting someone else, that's time-sensitive.

Deliver this feedback as empathetic as possible. If it can be delivered in a way that doesn't sound negative. If it's not necessarily your judgment being cast if it's more when you do this, or when you did this resulted in that. Then it's not about anyone doing something that was, let's say hurtful or you casting judgment on them.

It's more like this resulted. So we should work through this result or try to prevent this from happening in the future. And then it's less loaded.

Jeff: [00:13:01] I totally agree with that. That's great. I great point.

Scott: [00:13:05] I like those points. Jeff spot on to what you said. That if it's something that needs to be addressed immediately, you address it immediately. If it doesn't, I'm also the fan of not giving that immediate feedback for every little thing. Because I've been a victim over the years in my career where of leaders using the opposite approach. Every week or whatever, giving some type of feedback. And it really creates this vicious cycle of you see the Slack notification pop up with their name on there and, "Oh, great. What did I do now?" Because most leaders don't give positive reinforcement over and over again.

Most of the time it's negative feedback or constructive feedback. So when you see that name pop up, it creates this discomfort. Even before we have any idea what's going to be in there. You already have this feeling of, "okay, I had to do something that they're going to give me feedback on."

So I definitely believe in if you can wait to a quarterly review or three, four, five weeks to package a couple of different things. Again, minor things. One another thing that I would love to add in here is when giving it, I always like to start off with trying to get context. And asking for that insight and feedback of why somebody may have done something in a specific way or why they answered like that. Because I've seen many times in my career that there is a very good reason why they handled something the way they did, or they did something in the way they did. It's previous experience, a previous leader told them to do it this way.

They had the approval to do something in a previous example. In that opportunity, there isn't as much room for giving constructive feedback. It's really. "Ah, okay. That makes sense." we need to just now potentially change the policy or change what may be going on.

So instead of saying, "You should have done A, B, and C, it's really, "thanks for sharing that information." Going forward this is the new policy. And if there's any documentation that says otherwise, we'll go ahead and update just so everyone is on the same page."

But following into that question of when you give somebody constructive feedback, not always do they take it with a grain of salt or with a smile. They can sometimes get upset or show frustration with that constructive feedback. Do you have any tips of things that you can do when they show that frustration and that anger?

Jeff: [00:15:12] It's a great question. And Scott, I think one of the great strategies or tactics is having empathy as Tevi mentioned. But also as you mentioned is really understanding the context for some set of actions that maybe are not going well. I totally agree with you.

One of our values at Ambassador was to understand why. It was based on really understanding the root problem. Is someone going through a tough time? There are always so many things happening and you tend to know very little when you're working with somebody. Even if you're working with them closely. And it's not, they don't need to divulge or, they just shouldn't have to share any of those things, but there could be reasons why they're tired, acting out, or just not doing something well.

I've found that starting with empathy and then as Tevi said, explaining this is just not the way that we're able to do things. We're not going to want to do things like this, or this is not the result that we want. How do you think we can go about changing it? What do we think? What are some options? Or why do you think this is happening?

So I think I've tried to be less judgmental. As Tevi mentioned, instead of accusing the person, "Hey, you're doing a bad job." "Hey, we haven't really been getting the results that we've been looking for. I know this falls under you. What do you think? What do you think is happening?" And maybe go about it a little bit different way where eventually hopefully you get to the root cause. Which is something that is not getting done in a manner that we agreed upon. But without this is your fault, you screwed it up.

How you respond to their frustration and how you respond to them going forward, I think shows a lot. It's sad. Some people, the first time we have this conversation they're like, "I thought I was going to get fired." And I'm like, "no, you're fine. Let's just do better."

There are a million things happening in a startup that are not going the way we want it to go, but the goal is to improve. Let's just agree that we're going to try to improve. And those things, I think again, For us, we were relative, like I was a pretty new manager, right?

Again, it's just being transparent. Having an open line of communication and having empathy. "I know this might be hard to hear. It doesn't mean that you're not valued at this company, but we just want to address this thing so we can perform better. So we're all happier and better off."

Scott: [00:17:20] Yeah if I can throw something in there. Tevi please feel free to follow up after me. I also like to explain the why behind it. A developer pushed code without testing it and it took down the system. Obviously trying to find the context why they did it. Explaining, " Hey, by doing this and by having the downtime, it took out a client during the presentation and they lost something else." Or somebody lost a sale. This has an impact because the financials are A, B, and C. Giving them that understanding of why I think is very helpful. So they understand, "Okay, I did something wrong. Maybe I agree. I don't agree with it, but I understand the bigger picture. I understand how this action that may have been right or wrong impacts the bigger picture."

And in the future, if this opportunity comes again, having that bigger picture mindset will certainly help that person understand. I'm a developer and I want to push something, I understand if I don't test it or I don't ask somebody to review the first, then this could be the bigger potential impact. Tevi more thoughts?

Tevi: [00:18:22] You're both saying the same thing. I totally agree. Getting context is super important. Understanding the impact, which is part of that context is also important. You said something Jeff, I wanted to just zero in on, you said that someone thought that they might get fired or someone might think that they might get fired.

That's like a little bit of a warning flag where things are moving too fast and there's not enough actual communication that someone might think they're not necessarily valued or their one big mistake was like the nail in the coffin.

I remember working with someone who created this aura around himself. Where any conversation with him, someone was afraid they're gonna lose their job. And he never said anything positive. He never communicated what people were doing that was positive or what impact they're having. Everything out of his mouth was negative and people were sometimes fired. It was a bad culture. I know that Scott, you mentioned this ratio you try to give a certain amount of positive feedback every now and then.

But on a deeper level, what do you think is the right way to make sure your team has enough positivity and people are communicating effectively?

Jeff: [00:19:19] It's really tough. As we scale remotely, I think it'll even be tougher. One of the things that we tried to do, as you're managing managers, you are certainly removed from folks. Even as a leader. You can take some time to communicate and talk with them. But oftentimes there's a level of unfamiliarity. They may be insecure about what to say especially with employees who haven't been in a fast-moving or high-growth company. A lot of these situations are new and they're really only learning from their teammates potentially.

What we tried to do and what ended up working was we eventually created a culture where the team really helped each other out. This is the way that we do things. I think oftentimes that can go really well or it can also go poorly. But creating a scenario where your team really helps manage or bring people together in terms of, "You can go talk to Jeff. It's not a big deal." People used to say, "Oh, I thought, I couldn't even ask you a question or couldn't Slack you." And I'd say, of course, you can. So some of it you learn through other people in the team saying things like that. Sometimes, people, a're taking their experiences from a previous company.

And those situations are hard to understand until they're communicated to you. Someone brought whatever they had previously with them, and you wouldn't necessarily know what it was unless they communicated it. As we had a better, stronger culture, organizationally, we didn't see those types of issues because they got solved or got flushed out between peers instead of it ever being a question mark. That's what a great culture does. The people help each other out and they're all working together. Instead of having to wait until there is some sort of issue and then all the details flesh out at that point.

Tevi: [00:21:02] Yeah, that's so true about people have career baggage. Whatever previous jobs. Whatever the social norms were there. How they communicate. And it really affects the new job. You have to have a strong culture to help iron that out.

What are some good questions that maybe you ask somebody when they're not meeting expectations? How do you get the context?

Jeff: [00:21:20] I try to ask people how they think it's going. First and foremost, I always ask, how are you feeling? My strategy and my feeling is that a one-on-one for the most part is their time to share whatever they want.

And it's really my role to make them comfortable and feel safe to say anything they want. Whether it's about the business or it's just about life in general. I oftentimes say, "I understand that." Especially in a remote scenario and especially in COVID. We want to compartmentalize work and non-work and family, but the reality is it's all merged together right now. And we understand that. You're not getting sleep or some other issues happening. There's so many things happening to everybody right now. A lot of people have a lot going on and they have for a while.

So first and foremost, I just want to give them the opportunity to say. "Hey, yeah, it's been a really crazy week or, I know I've done X, but I won't do that." So try to let them identify if they think that they've underperformed or missed the mark on something. Because I truly believe if a person is maliciously not doing something then they probably shouldn't be in the organization. And every other scenario, the goal is to just incrementally improve or to adapt. And by that, for them to recognize we should do better and then start working towards doing better or improving.

To me, it's pretty quick, whether I think it's malicious or not. And hopefully I'm right. I like to think that I am, but err on the side this isn't malicious. People want to do well. There's something that for whatever reason happened. So then the next question is, "What can I do better to help? Let's achieve this goal or this outcome." So that's how I tend to think about it as what can I do? I think oftentimes people will say, "I really wish I had more direction or I really didn't realize X or Y or we don't have enough resources, or you also told me to do these 10 other things."

A lot of it comes back to context and just fully understanding the scenario and making sure that everybody's on the same page. So that ultimately, we're all working together and we have, similar expectations and what the priorities are. And what the goals are in those cases.

Scott: [00:23:24] Probably the last question that I have is probably more of a recap of kind of the conversation. For new leaders who are going to be leading remotely going forward and companies starting to grow once COVID ends, two or three tips for giving constructive feedback remotely.

Jeff: [00:23:41] I think the biggest and Tevi and nailed it earlier. I think it's important to do a video call in any serious conversation. Tone is bad. As a leader and as someone who probably thinks they're busier than they are, I'm the first to admit that I will just start typing and I'll multitask and those things get taken the wrong way. Not good. For someone who's doesn't know you, or maybe is scared to speak up, instead of them saying, "I didn't really understand your tone or what are you trying to say?" They just take it as a negative. Then no one wins. You're not actually acting in a way that you intended, and it's not being received in a way that you intended. And the person feels probably bad about it.

So it's really everyone loses. That's certainly the worst outcome. Also, personally, going back to being a poker player, I want to see the person's face. And they should see mine, right? I think you can show a lot of emotion. Ideally it's genuine. And that helps both read the person, but also to communicate non-verbally at times as well.

So I think that's a really important tip. The other piece of feedback that I would add, and Scott, I think you mentioned this and I really like this, but it's giving a lots of encouragement and positive feedback. Letting people know they are on the right track so that it's not you're only getting hit with bad things.

I think that's a challenge for a lot of founders. They usually have a high level of drive and have expectations that everyone's going to work like them. Which is certainly what I did many years ago. You realize everyone has different incentives and different values. No two people are going to be identical and most likely if you're a founder, no one should actually care as much as you and in many cases. So you have to put that aside and not compare someone's impact or performance to what you would do because that's not fair for anybody.

A lot of founders, even in groups that I'm in, they'll always allude to things like so and so is not doing it like I would do it. Yeah, that's probably true. They're not because it's probably impossible for a lot of reasons and not necessarily the right thing either.

Scott: [00:25:41] Completely agree. Tevi any last questions?

Tevi: [00:25:43] No, thank you so much for joining us Jeff and sharing your insight, wisdom, and feedback.

Jeff: [00:25:48] Absolutely. Thanks for having me.

Scott: [00:25:50] Thank you so much for joining us again. And everybody until the next episode, have a great day.