Leading Through the Unknown with Guru

Anne, Chief Customer Officer at Guru, shares five leadership practices for uncertain times: scenario planning, maintaining a 5:1 ratio of positive to negative messaging, frequent direct communication, using decision frameworks for action, and investing in culture. She draws on examples from Gusto, Zendesk, and Guru's own 'lift your spirits' week.
Chapters
All right, I know we've only got 20 minutes together, so I'm going to go ahead and get started. I want to make sure we've got time for some Q and A at the end because I want this to be a conversation. All right, so our session today is on leading through the unknown, which for me has never been a more pressing topic given how suddenly things have changed for all of us. And so I want to have this really be a conversation on how we can all lead through the unknown, especially since we don't have a clear idea of how long the downturn will be, how severe it will be, and what that will mean for our teams, our companies, our customers. So first, just a quick introduction. About Me I'm a Bay Area native. I started my career in consumer Internet at Blue Nile and ebay, so lived through the dot com boom and bust, then moved over to B2B, so spent time at SurveyMonkey, five years at Zendesk, from when we were a private company to a public company and then now I'm at Guru as the Chief Customer Officer. And I also sit on two boards of SaaS companies. So Gusto and Asana. So love the SaaS space and have a perspective certainly in terms of how teams of every size are dealing with the uncertainties right now and definitely want to share some of those insights and examples with all of you. Also important to know about me. I've got three kids, great husband, we are sheltering in place in the Bay Area, and I actually am enjoying more time with my teenagers and hope that they are enjoying their time with me. So this journey that we've been on to build enduring companies and businesses has never been necessarily easy. Even in boom times, there are challenges, the trajectory is steep, there's turns along the way, and now we find ourselves looking at potentially a much steeper trajectory. Maybe the turns are even more uncertain and the decisions are potentially harder for all of us. So as leaders, what does this mean? It means that more than ever, every day, people are depending on us, depending on you, to make the choice to lead. And that's an important thing to emphasize here is a choice on how we show up, how we show up for each other, and how we show up for our teams. And something I really want to just take a pause on and make sure we're all clear on is that leaders don't have to be managers. It doesn't mean that you're a people manager to be a leader. This is an important point because I think during uncertain times there's an opportunity for every single person, whether they manage somebody or not, to step up and be a leader. So if the definition of leader is not necessarily a people manager, what is it? And I want to go through sort of five ideas of what it really means to be a leader, especially during uncertain times. So leaders imagine a way forward. They maintain optimism, which might seem like a hard thing to do during these times. They communicate directly, they take brave action, and through all of these, they really, really end up helping people bring their best. And that's really what our teams are depending on us to do and our colleagues and our customers right now. So for each of these, I want to share either an idea or a tool, something that you can take away and start acting on each of these concepts of leadership. So imagining a way forward so during uncertain times, we can all find ourselves getting stuck, right? The landscape has changed overnight. And so what we thought might happen this year, how we thought we might reach customers this year, how we thought we might grow our teams this year has all changed. And so how do you imagine a way forward when the landscape and all your assumptions are no longer the same? So the first thing is see the current reality and then project out what might the scenarios be. So the teams, all the teams that I've worked with are planning for both the best case scenario as well as the very worst case scenario. So seeing clearly what the possibilities might be starts to open up ideas that maybe you haven't considered before. So for your business in SaaS, maybe you haven't offered a free product in the past, or you might not have offered a free service in the past. Now's an opportunity to explore things that maybe weren't part of your business model before. So how can you see new opportunities? The more that we can see these new opportunities, the more we can help our teams believe in different ways of approaching challenges and uncertainty. Another thing that teams I'm working with are doing is really looking at how their operations have changed. So you might be seeing greater volume for certain teams like your support team. And maybe you're seeing less demand in other areas. For example, a slowdown in sales. Is it a possibility to shift some of your team from one function to another, even if it's temporary? So the Gusto team quickly scaled their sales folks to be able to serve customers who are applying for ppp. And that was just a huge boost in both service to end customers, but also team morale. So helping your team believe in new ways of doing things also helps them think of new ideas and new approaches that they can act on. And then it comes full circle, right? Once you take action, you get feedback and you can see more possibilities. So beginning with imagining a way forward. And those actions can also lead to more positivity and optimism in terms of what's possible, even if the assumptions on growth have changed for your company. So this idea of optimism is also really critical. How do you maintain optimism during all these uncertain times? Something that I find so useful to remember came from the research that Huggy Rao and Bob Sutton did for the book Scaling Up Excellence. And that is this simple equation that as humans, five positive experiences equals a negative experience. Essentially, it takes five positive things to neutralize a negative. And during these times, so many of the things that we are hearing and experiencing are negative. And keeping that in mind, we need to shine a light on the things that are positive. And I don't mean sort of fake positivity or putting a positive spin on something. I mean genuinely looking for the good that is all around us and in our team. So are there team members who are stepping in and helping other team members? Can you showcase that? Are there people on your team who are going out of their way to help customers? Are there people on your team who are helping former colleagues who've lost their jobs? How do you share those stories more frequently so that you're shining a light on what's positive? And remember, it takes five to neutralize a negative. And so you've got to look hard for that sixth one to also tip the balance towards optimism and hope. The next thing we need to do is communicate directly. And for me, that means frequent listening and constant sharing. So under listening, there's some questions I really like to ask. The first one, whether it's in one on ones or in kind of team meetings or. I also really love having open office hours. So the first I like to ask is, what are you excited about? And that can also help you shine a light on the positivity in your organization. The next very pressing for us all right now is what are you worried about? And that can often surface unexpected answers and areas for you to spend time on with your team. What have I not asked that you'd like to share? I really like that question, too. There's sometimes things on people's minds that need a little bit of nudging to come out. And then if you could change one thing, what would it be? And these are ways to get great ideas that are part of all of our organizations and part of every team surfaced and that we can act on in Terms of constant sharing, really looking at how are you communicating with your organization and adjusting frequency. So we went from a monthly town hall at Guru to every other week. It's a little less polished than it used to be, but we're talking more often. The Augusto leadership team is meeting every day. And so depending on the size of your organization and your team's needs, really look at adjusting frequency. Think about adding new formats for communication, especially with all of us working remotely. The Zendesk leadership team filmed videos that they sent out to employees to give context, to share what was going across every function. And they actually found that employee engagement was higher right now than it's ever been because of these new formats of communication. Bring your cross functional team members together. So it can be really easy to get into patterns, especially with remote work right now where we're just having one on ones within our own function and we're just trying to keep up with our own team meetings. But we're missing that serendipity that can happen if you were working together in an office where different team members could get context and hear what was happening across the organization. So really creating opportunities for your cross functional team to come to together, to stay aligned and to keep working productively, more important than ever is give context, then give it again. So especially for if you're on an executive team or a leadership team, the decisions that you're rapidly making are, it's so important to give that context and be transparent on how you're making decisions and why you're making the decisions. And then last but not least, subtract what's outdated. Take the opportunities to stop doing things that aren't working and that will free you up to come up with new ways and be creative and have fun with it. In order to take brave action, we also need to be decisive, right? And right now, with uncertainty and with some really hard decisions in front of all of us, again, we can be stuck and we can hesitate on taking action. So, so something I really like is just pick a decision making framework that's going to work for you, your team, your leadership team. A simple one I really like is laying out the different options and being really clear why you like a certain option, why you don't like a certain option. And then probably the most critical line in all of this is how you're going to mitigate risk with each of the options. And you can come into hard decisions, for example, delaying compensation changes. That was one that we as a leadership team at Guru were tackling. And as you can imagine strong opinions all around given how dearly we care about our team. And so by laying out the different options and being really clear on the pros, the cons, and how we would mitigate risk, it was just much easier for us to get behind a decision and act on it. And last but not least, as a leader, you are here to bring people and help bring them together and help them bring out their best. And that really comes more than ever to your culture and investing in your culture. And for many of us, that right now, it might not be funds that we're investing, but rather our time. And so the components of culture that are more important than ever are your mission and purpose. That's why everyone on your team is here. So how do you make sure you're focusing everybody on your mission and your purpose and the change that you're creating in the world? How do you look at the norms, the language and the programs that you have that support your culture and get creative with how you implement them in an all remote environment? So something our team at Guru did was create a lift your spirits week. So we had dress up day, we had baby picture day, shared all of this on Slack, and these are things we probably wouldn't have done when we were working in our respective offices. So how do you create new programs and new norms that support your culture during this time? And then last but not least, your values? How do you make sure values are part of every decision that you're making, that they're lifted up and celebrated, and that you're talking about them probably more frequently than ever. So in a timely way, embrace the journey is one of our values at Guru. And now we really recognize that embrace the journey is both about when things are great in the economy and also when things are not great in the economy. And that it is. We're building for the long term. And so more than ever, we talk about embracing the journey and how we're here for each other. And I'm sure that in each of your organizations you have those core values that are critical. So just make sure you're talking about them, showcasing them, showcasing how different employees are living your values. And that will really inspire everybody to bring their best. And I would say a bonus one on leaders is leaders find a way to be kind to themselves because there's a lot of pressure on everybody's shoulders right now. There's a lot of tough decisions you're trying to make, and there's a lot of uncertainty that you are trying to make your way through. And so my kind of kindness to myself is I've got a standing one on one with one of my dear friends, Amanda, that we worked together at Zendesk for many years. She's now the chief customer officer at Figma. And we don't always use the standing one on one because we get busy, but it's just such a great opportunity to compare notes, to have a safe place to talk about both the challenges and, and the small wins and really just make sure we're there for each other. So whatever that might be for yourself, to be kind to yourself and to have a safe space to really contemplate all the challenges in front of you, I think it's really, really important that you make time to do that for yourself. And with that I would love to answer some questions.
So yeah, you've got a few that have come through that have been really good, right? Yeah. The first one is when you're communicating directly now, which obviously is harder since everyone's remote. Like, what do you recommend as part of the leadership on how to communicate? Maybe tough news in uncertain times? Do you recommend doing it one on one or more during like an all hands?
Yeah, I would say that's a great question. And I would say it probably depends on the news and who it's affecting and potentially thinking about multiple opportunities to communicate and then follow up. So again, depending on your team and your culture and your communication style, you may want to think about written communication to give more context and give people time to absorb the decision, the why behind it, the changes, and then have an all hands where you reiterate those points, how you made the decision, open it up for questions. Some people might feel comfortable asking questions in that format, others might not. And something we do, I mentioned it a little bit, but we do office hours. I really like that concept. Both especially now in remote. We used to do that after our town halls when we were in our respective offices at Guru. But it's just a two hour open open time for anybody to join. Sometimes it's just one person, sometimes it's a group of people who join and different leaders on our team host the office hours. So those are really good to follow up, especially when you've delivered hard news.
No, I love, I love the office hours. I think I'm gonna have to steal that over here.
No, it's not stealing. It's all sharing good ideas. We have to learn from each other.
That's good. I definitely agree with you as well. I think, you know, it's helpful to maybe over communicate A bit.
Right.
At times now during an all hands especially even if it's tough news or if it's not tough news, just so everyone's on the same page, like I know. So obviously Jason, who's like our CEO and founder has been doing what he calls a daily Jason. He emails everybody at the top of the morning with like his focus for like either the day or the week. And then obviously we like reinforce it in like our daily all hands. So something like that we've seen has worked a little bit as well. Another question related, in your opinion, do you think there is such a thing right now as too much communication?
Yeah. With how quickly things are changing, I don't think there's too much. Right. You're, you know, I would, I think you would rather err on the side of more than less. And then if you're getting feedback from your team, back to that listening part. If you're getting feedback from the team that they're like got it. We heard the message, then you can adapt. But I think in this current environment, because things are literally changing on a week by week basis, whether it's in our business conditions or whether it's in the shelter in place guidelines, depending on where your employees are. I just think there's a lot on people's minds.
Yeah, I agree with that. Another question that's a bit related to the topic specifically amongst just your leadership team. How have you changed communication at all now that you know, you're probably used to having, I imagine like face to face meetings and check ins. How are you guys doing that now that everyone's sort of remote?
Yeah. So we have always had, you know, multiple offices at Guru. We have one in San Francisco and one in Philadelphia. And so I think we already had some practices in place of, you know, zoom meetings, whether it's one on ones or team meetings. But something we are doing differently and have introduced is we now have a bi weekly meeting for all of our people managers. And we had programs for our people managers before, but we're finding now more than ever making sure our people managers have a chance to get together, share what they're seeing and hearing, ask for help or context or resources from the leadership team is really important. So I would just say thinking about now that you're all remote, what are the connections that maybe used to be easier that are hard now and how do you create new formats again to provide solutions for what used to maybe happen naturally in drive bys or context within an office?
Yeah, it's hard to do an office pop in when there's not an office to pop into. All right, last question. Thank you so much for your insights. The last one I want to get your opinion on here is how has your job changed as both, you know, member of the senior leadership team at Guru, but also as a board member, given everything that's going on in the last six weeks?
Yeah, I think the. I would say. I don't know that I would say, like, the jobs change so much as the two things I think that are more critical than ever are health of employees and health of customers. You know, health and well being. And so I would say across the three companies that I'm involved in, that's what's really bubbled to the top of all conversations and priorities is, number one, what are we doing for every single employee to support them during this time and how do we make sure we're really listening to what the needs are, that we're flexible, that we're supportive, and that we have a really good pulse on how the team is doing? And I think all three companies have put that as their top priority. And then the second is related to that because I think employee happiness also has to do with, like, are we serving our customers well and how's the business going? Is how are we being creative to meet our customers where they are? And that's different across each of the businesses, but really reimagining how we build those long term relationships just knowing that so many customers are struggling right now. Yeah.
I think a lot of what we've been hearing today is just customer empathy. And I think you said it best, right? Like, take care of your team, take care of your customers. I think those are two really great priorities to keep top of mind right now.
Yeah, absolutely. And I think those give us, you know, that gives us the optimism and the positivity and the hope during these times. Right. The more that we're serving others, I think it makes the, you know, broader environment and the challenges everyone's facing a little bit easier to deal with.
Yeah, exactly. Okay, well, we're sadly out of time, but thank you so much, Ann, for your insight.
Thank you, everyone for joining. I know with the webinar format, I don't get to see all your smiling, awesome faces, but I appreciate the time you spent with me today and look forward to following up in different formats.
Yeah.
Thanks so much, Anne, for joining us.










