CPO Series: Working with Your Board – Tips from a CPO Turned Board Director

CPO summer series Shelley Perry

How should a CPO work effectively with their board – as partners and sounding board? Hear some of the practical tips and advices from an experience board member who was on the other side of the table as a former CPO / tech executive.

Shelley Perry is a world renown scale op expert with more than 30 years experience as operator, board director, venture operating partners and seed investor. Currently, Shelley is a managing director at ScaleLogix Ventures, and she’s also on half a dozen board.

This Webinar Covers: 

  • Why it’s important to learn good board practice
  • 5 tips to address common challenges working with the board
  • How to take the theory to practice

Adopting a board practice has many benefit

  • Effective Communication Increases Board Confidence of the Entire Executive Team
  • Board Meetings are Practice Sessions to Deal Preparation which Improves Deal Processes
  • Interactions with Board Members lead to Future Board Roles
  • Non-CEO C-Suites with External Board Roles Increase future Promotions and CEO Roles

5 tips to address common challenges (as a new CPO working with the board)

  • Understand and Empathize with your Audience – Your Board “Customer”
  • What Got You Here Won’t Get You There – who is your team?
  • Your Product Section is Part of a Larger Narrative
  • Financial Speak, Not Product Speak
  • Picture is worth a thousand words (charts!)

Key take aways

  • Get to know your Board Members and Network with CEOs and Board Members
  • Embrace your C-Suite Team
  • Dry run the material with a Non-Product Person. Let them buzz you every time you use a Product jargon
  • Improve your financial acumen – tie your product strategy to financial impact
  • More importantly, enjoy the journey and pay it forward!

The full transcript is provided below.

Read the Full Transcript

The following transcript has been altered for readability. 

Becky Flint: Today’s guest, Shelley Perry. Shelley is a world renown scale op expert with more than 30 years experience as operator, board director, venture operating partners and seed investor. Currently, Shelley is a managing director at ScaleLogix Ventures, and she’s also on half a dozen board. Without further ado, off to you.

Shelley Perry: Thank you. Thank you. I see lots of familiar names in the chat, so I’m happy to see those names again. I want to talk to you a little bit about why you want to pay attention to this. Obviously you’re attending this so you’re interested, but I want you to think about adopting a board practice. What I mean by that is something very similar to a yoga practice. We’re constantly evolving, for those that do yoga or try to do yoga like me. We’re constantly evolving our practice and it’s something that we have to continue to work on. I myself still have to work on it. What are the benefits to you for adopting a board practice? Look, effective communication increases board confidence. I’m on boards. And when a management team is presenting, even if what they’re telling me, I don’t love, I have more confidence in what they’re telling me when there is an effective presentation when the team is cohesive.

It helps increase the board confidence, which helps you get funding, helps you collaborate more. Whatever that is, it increases that. Board meetings are practice sessions to deal due diligence and presentations. If you can present well and to your strategic direction, to a friendly group that is there to help you, then you’re actually going to present better on any kind of deal transaction as well. So they’re practice sessions for that. Interaction with board members really lead to future board roles. Most CPOs, as they accelerate through their career, want to add a board role to their CV. And there is not a greater opportunity than presenting well to your board members and then using your board members as springboards and network introductions to becoming a board member.

And then last but not least non CEO functional leaders, C-suites, any C-suites including product, having an external board role is a boomerang to becoming a CEO or any other advancement that you want. So this is why you need to develop a board practice. Now, next slide, I want to tell you why I am so passionate and when Becky asked me or someone asked me from the Dragonboat team, love Dragonboat by the way, asked me to present I said, “Absolutely.” I’m super passionate about this topic, and I’ll tell you why. You see her sliding under the table? I’ve had the fortunate experience to be on over 10 boards myself as an actual board director. I’ve advised over a hundred boards. I’m often called in when there is a problem with product, with the product, with growth, whatever that is.

And I’m often called in to help translate to the other board members what the product and engineering teams are actually trying to say. So over a hundred advisors to boards where I’ve been in for a series or period of time. And because I also spent five years with Insight Partners, super excited that they’re also sponsoring this. I’ve had the opportunity to be, I think I put 200, to be honest with you I think it’s more, where I’ve been in deal processes and CPO interviews. And quite frankly, I became super passionate about this because I wanted to keep the CPOs that I was helping to hire for the insight portfolio companies in their seat. Because often when CPOs couldn’t present or a candidate couldn’t present to a board, the board thought that they actually weren’t qualified when in fact what they needed to do is really just up their game on presenting to the board.

What I want to do next is go over, I’m going to give you an overview, thank you Becky, of the five tips to address of common challenges that I’ve seen. And I’m talking fast because I want to leave room for questions. I’m going to go through the material and then we will have questions. You may or may not have these issues, but I had to in 15 minutes come up with those common things. I’ve broken into the five tips into three different topics. One of them is understand and empathize with your audience. I think that product people sometimes, when they go into their C-suite roles, their first C-Suite world, they’re like, “I’m an advocate for the customer.” You’re an advocate for the stakeholders of the company of which the board members are part of.

And the board members have a very different view on their role as in fact, to preserve the assets of the company and preserve shareholder value, which means a lot of different things. So you have to understand and empathize. Actually, what got you to the role that you’re in today is not going to get you there. We’re going to talk about that. Your product section of your board deck is actually part of a larger narrative. It does not stand alone. I’ve walked into so many board meetings where the product person is at the end and they’re talking Swahili, so we’ll talk about that. You have to learn financial speak. It is the universal language of business, versus product speak, so we’ll talk about that. And last but not least, a picture is worth a thousand words. I’ve recapped this. I started to go into the detail of one of them, that was my mistake.

But what I’ll do in each one of these very quickly is go over the … I think there’s a buildup on the slide. Sorry about that, Becky. But I’ll go over each tip. I’m going to give you an example, I’m going to give you an action. Understand and empathize with your audience. The board members are actually, they’re not full time. They’re not operating the business. They’re not running your business, you are. But most people go in and they think a board, a board is made up of individual people. And through this series, you’ll see, you’ll have some board members who might be from series A, series D, they might be independent. They might have come from a different background, a different industry, whatever that is. They do not run your company and they are individuals. Look up their profiles, follow them. Put up Google search, follow them, care about who they are, understand their perspective, use their network.

But before you go into a meeting, know who you are talking to. These are stakeholders. They’re not a board, they’re individuals. Please do that. I do encourage everyone to make a board profile, make notes, interact with your board. If you are on a public board, that sometimes is a little bit harder, but certainly private boards, they’re there to help you. So please understand and empathize with your audience and know that they are not in your business every day. The example I like to use is a doctor. You all go to the doctor and I’m probably a little bit biased on the US experience, but that doctor does not remember you specifically, but they’ve written notes before you were there and they’re refreshing their memory before you walk in. Now, when they see it, they remember, but that board member is not running your business full time, so understand and empathize with them.

The next tip, number two is this one’s a big one. What got you to the role as CPO or aspiring to CPO is not going to get you to the next level. And one of the things that you have to remember, and this comes across in how you interact with your board and how you present as a management team is that as you take on your first CPO role, you are no longer part, your first team. Your first team is the management team. It’s actually not the product team. And I’ve walked into board meetings where the CPO bashed sales or bashed marketing, or really just wasn’t cohesive. And understand your new team, when you take a C-suite role, is in fact the C-suite, not the product team you’re leading. Prior to getting that C-suite role, you were interviewing with people who are product people, and they wanted to talk product language.

Guess what? Everyone else in that C-suite does not understand the industry jargon nor do they want to, or should they. It is your responsibility to become a member of your new team and really gel with them and understand and empathize with your team. And the reason I say that, how does that relate to the board? Because it comes across in the presentation when a management team isn’t cohesive. It absolutely comes across. And if you don’t feel like you’re a part of that team, think about how that comes across in your presentation. So that’s that. Next one, next three. This. This one is great. Your product section is part of a larger narrative. This one’s particularly close because I’ve just gone through a board season I call it. I’ve been through a lot of board meetings and I’ve been called into a lot of advisory board meetings because in fact, the market changed very quickly.

And so what happens is you have to understand the board presentation and the board meeting, these are your CEO’s boss. It’s a CEO narrative and your section isn’t about am I presenting the best product roadmap? It’s really about doesn’t support what the CEO is saying? Is every section of that board deck, including mine as a product person, does it actually form a cohesive story? And often the product section is last. So they’ve already heard, maybe sales is slowing, maybe sales is growing. They’ve already heard marketing’s lead generation. They’ve already heard customer success or customer services update. So let’s just say sales is slowing and you walk in and go, “Oh my gosh, I have this new product. And we’re building this new thing,” and you’ve not addressed how you’re actually addressing why sales is slowing, you sound like, “Let them eat cake.”

And if you don’t know what that is, it’s Maria Antoinette talking about people being hungry. And then she said, “Let them make cake.” So you literally sound like you’re coming from this like you’re not in touch. The opposite is if you are selling a lot and sales is doing great, and then you walk in with a product section to say, “We have to build all these things to get and keep customers,” you and I both know that may be true, but it’s so incongruent with the rest of the presentation that you need to marry the story and help the board in different terms, understand why you have to spend money on certain pro features or why you’ve chosen to prioritize something in terms of the rest of the presentation. So really again, understand it’s part of a much larger narrative. Make sure you know what your peers are saying, if you’re not in the whole board meeting, make sure you’re reviewing that. Make sure it’s cohesive.

Next number four. Okay. This one is my absolute favorite. Product people specifically, you go to all these conferences, you go to all of these sessions, maybe even including this one that we’re in and you start talking about horizon one, horizon two and all of the code refactor and the next release. Guess what guys? That means nothing to someone in a business. And it is your job as a CPO to translate that to business terms. I’ll give you an example. You may need a new UX, but please don’t walk into the board and say, “I need a new UX.” Why? Because it’s ugly. It’s not it. It’s not. I’ve heard these things. I’ve literally heard these things in board meetings. Please say we need a refreshed user experience in order to facilitate new sales.

Because sometimes it’s new sales. It’s not that it doesn’t work post when they do it, but you have a competitor that has a sexy UX and it’s actually hurting sales. And you have the data to support that. Or maybe the UX is not hurting you actually on the sale because it looks sexy, but when they actually buy it’s a retention issue. So don’t walk into a board and go, “I need a new UX,” right? You walk into a board and say, “We need to increase retention or increase sales. And we’re going to spend this much money of our allocated budget to do that.” That’s what you have to say, that’s it. You have to translate it. It’s your job as a CPO. Now here’s the deal. You also have your leading, your second team, your first team is now the C-suite, your second team is your team and you’re leading your team.

You need to know all of those words underneath because you need shorthand to get to a massive amount of data in order for you to actually be able to present. So you need to understand those words. You need to use it internal to your second team, to very quickly get to the bottom of things and to manage and scale a team. But you need to learn to translate those words into the way that the business world actually interprets them. This is not unique to product, but product people have been under this oppression, “No one understands me,” and then they go, “You must understand my words.” No, just no. Learn how to translate them. One of the best ways to do that is make friends with more finance people, make friends with more CEOs, make friends with board members that will actually say, “What are you trying to say?”

And better yet, go find a product person who is now a CEO and ask them what they did to actually start changing their language and how they’re using words to do that. That’s how you can do that. And the last one, tip number five is this is how you present the information. So most of the other things are, make sure you know your audience, how you’re presenting, how do you make people feel, make sure you’re using the right words. And now please, please, please, please present information pictures. And I don’t mean pictures just in terms of pretty pictures. One of the samples that’s here that is really, really important is the change over time. As a board member, one of the things that frustrates me so badly is I want to understand what’s changing. Did you do what you say you were going to do and are things actually moving?

And if I have to go back to prior board decks to glue it together, I have less confidence in you as a leadership team and specifically as a CPO. So I want to understand what are you showing me in relation to the past? Because the past is the greatest indicator of the future. And then I want you to show me what that future looks like all in a slide. Because if you come and you tell me that let’s just say, you’re going to spend twice the amount of money on innovation, but yet in the past, you’ve never been able to get it up more than 5%. Guess what? I’m not going to believe you. And maybe you seeing it would actually got you to revisit it before you presented it as well. So this was a tip and I can tell you this as an operator, I learned this tip because we don’t make presentations full time.

I spent a lot of time with the consultants who were former consultants at Insight Partners when I was there, they were on the onsite team and they really helped me understand this. I did not have to go get an MBA [inaudible 00:15:41] that. Presenting this information in a way that your board consume it is really important. So to spend time, not just on what it says, but history over time and relative values so can I can understand the impact and I can have confidence in it. And I don’t have to spend a lot of time digging a lot of other decks and piecing it together myself. Those are the five tips that I have for you. There’s many, many more, but I think I’m even over my time. Quick summary here, get to know your board members, network with CEOs, expand your network, look at your network.

If it’s all product people, get out into the world. Embrace your new C-suite, really super important. Dry run your material with a non-product person and actually bring that buzzer every time you say product jargon and stop saying it. Use business language to describe what you’re trying to do. It is underneath. Does that mean you are less of a product person? It actually means you are a better product person. That’s what makes a CPO great, by the way. Improve your financial acumen. I have an unfair advantage. I have an undergraduate degree in accounting. I love financials. However, you don’t need to have an undergraduate. You don’t need to know all of the accounting things, but you do have to understand financial terminology and how the decisions you make are actually impacting the value of the business, good or bad. More importantly, enjoy the journey. And as you learn it, pay it forward and tell other people.

And I just put a link there to a book that I refer people to a lot of times, which is a financial intelligence book. It’s a really good book for non-financial people to embrace their first understanding of understanding financial jargon. So that’s it, pretty fast. Hopefully that helped.

Becky Flint: I’m sure audience have lots of questions. Some of them are already pop up. I’m going to stop sharing and pick some of the audience questions. And Donna asked, “I study your points on being data driven and to have a sound foundation on your product strategy. Using the product KPI is rare, and I can see how this can help directly communicate to the board. Is there a way of working with a common vocabulary that becomes a business meaningful? What is your board experience?

Shelley Perry: Look, every company, there’s a little bit of different vernacular, and I think first you have to agree to it with your C-suite team. And then you have to acclimate your board to the terms that you’re using. Unfortunately, there’s not a single common set because every person that’s coming to a C-suite is actually coming from different backgrounds. So I do think that each company needs to align and then consistently use it. So I do think the onus is on the C-suite to come up with that vernacular and then educate or share with the board how in fact you’re going to be presenting that information.

Now I want to address one thing. You absolutely have to have all of the data. I’m super data driven. For any of you who know me, I am passionate about data. You have to have all of that data, but guess what? That data is what you need to give you and your team confidence to know what it is that you’re prioritizing and how you’re using assets of the company and knowing the data behind it gives you more confidence in your presentation. But what you need to do is boil that information up to a really small set. We all know that learning to say something simple is actually how you know something. So please do not give the board all of the detailed information that you use in the back. They may rejoice. If they’ve never seen any data from you before they may get excited about it, because they’re like, “Oh my gosh, finally data.” But that will wear very quickly. You actually have to get it to a summarization of how it relates to the rest of the business.

Becky Flint: Right. And I totally hear you. Related the question around interaction with the board member is how do you build relationship and trust with the board member? How do you get to know them personally? Because obviously a lot of times they come to you, get a funding and boom, you go to a board meeting.

Shelley Perry: One of the things I tell people all the time and I have to reread this, because I get very focused, go over and read, if you haven’t done it earlier in your career, go read How to Win Friends and Influence People. Because in general board members are human. Play to their ego, ask them for advice, ask them for feedback on your presentation, follow them. Say, “Hey, I saw that you just invested in XYZ company,” or something, but treat them as humans like you would any other network connection and you got to work at it.

Becky Flint: Right, right. So many interaction questions here. So another one is around, how could someone manage unrealistic expectations from the board, like launch a new product that will likely fail? How do you push back without causing friction? Very interesting conversation here.

Shelley Perry: Always is. Look, by design product people, earlier in our career, everyone says, “You got to learn to say no.” And the worst thing is … Okay, that’s great. Tell a junior product person that, but as you progress in your career, one of the things you have to master is facilitating and persuasion. If you are getting all the way to the board that you think a product is going to fail, you’re failing actually convincing your C-suite first. So start with that. It should not be the first time that you’re actually presenting that to the board. But the way that you do it is with data. Don’t make it personal. Don’t make it specific. Get the data behind it. Show the facts. There is not a board that I’ve worked with that when you don’t show the facts.

And businesses are bad, they’re not always good. But the board doesn’t always want to hear things good. What they want to understand is what is my risk exposure? What are the options? Let’s start talking about them. So you have to start to learn to present information that isn’t lovely all the time in a way that builds confidence in a way that persuades. But do not bring that to the board meeting. You resolve that with your first team, which is the C-suite. And then you go as a united front to the board with the information and how you’re going to deal with it.

Becky Flint: This is so critical, the meeting before the meeting and alignment. You have to build alliances and who else can have the alliances with that? Speaking of alliances, is something interesting. I haven’t thought about this. Laura asked, “What’s your tip of connecting with the board members, especially they usually interact with CEOs and other quote-unquote business people a lot more. How do you reach out to them directly? What’s the best way to go about it?

Shelley Perry: It always boggles the mind to me that people don’t reach out. Again, I want to be clear, you have to be careful with some of the public things because there are things in terms of reaching out to them. But in those you can do it indirectly through commenting on their LinkedIn and kind of things. Some of the advice I’m giving you is very specific to private. I have a partiality to growth stage companies in private, so some of my stuff veers toward that. But reach out, reach out. Have you just reached out? You’re not violating the CEO or anything else, you were reaching out for advice. How about this? “Hey, I see that you actually invested in this other company. Could you connect me with this CPO of that company?” Or, “Hey, I know you’ve invested in five companies,” because most investors actually have their portfolio on their pro profile, “Could you introduce me to one of the CPOs that you really like in there?” Ask them for something, be very specific, but reach out. Have you ever done that? It boggles the mind why people don’t do that.

Becky Flint: There’s a question actually we got asked a lot recently, is that what are your tips, especially as a board member, during these uncertain times?

Shelley Perry: Look, I think that the tips are, and this is really important, let’s say your roadmap or your company’s strategy is staying the same. I want you to hear me. I want to hear that you’ve revisited things and that you’re staying the course or that you’ve changed the course. I want you to acknowledge the fact that things have changed. And then I want you to tell me what you’ve changed or if you didn’t change it, why you didn’t. Address those things. And I think one of the things that is just really important is that C-suite thing going in and agreeing, some companies need to preserve cash. So what are you collectively doing as a team? And every team member, and I say team, meaning head of sales, head of marketing, CEO. What is every team doing to contribute to actually preserve cash?

Because it’s never just, “I’m going to cut product,” or, “I’m going to do this.” You have to start cutting initiatives that cut the thing. Or maybe you’re in a growth mode because there’s actually companies that are growing right well during this. And it’s like, “How are you taking advantage of this and how are you going to maintain this recession proof thing?” So use data and acknowledge that you understand the market conditions, talk through the options of what you’re going to do, why you’re doing that. And if you have board members like myself, who’ve actually worked and been in leadership positions for three recessions, ask them their advice.

Becky Flint: What a great way to connect these pieces together. The relationships, the data, and then communicate the business languages. I’m going to wrap up with this Q&A session with one last question, which we asked every of our guest, which is in your mind, what is a couple of things, one or two things that differentiate a good chief product officer versus a great chief product officer?

Shelley Perry: Look, I think what differentiate great chief product officer is that if you talk to a board or you talk to a C-suite or you talk to their team, each one of them will describe that individual in a very different way. They will describe them as being a strong business acumen, good presentation, a lot of charisma. The C-suite will be like, “Team player, willing to give, understands my pain.” And their team will talk to them about the good mentor, helping me understand how to advance my career. And so you have to be a chameleon. And I think over any role in software specifically, and I think most, but I know software the best, is you have to be a chameleon and you have to represent yourself differently, not disingenuously, but differently to the stakeholder group in which you’re in. And as a product person, you are the glue, therefore you interact with a lot of different groups. Make sure you’re adjusting your presentation style for the empathy of those stakeholders. That’s what makes a great CPO.

Becky Flint: Wow. This is probably one of the most unique answer I’ve heard. And it totally makes sense. You don’t just have a one leadership style. You have to adapt to your audience and who you are working with. Amazing. Well, unfortunately we’re out of time. This is just so fun. And I wanted to wrap it up. Shelley, you shared your contact information. This is recorded. We’ll share out with everyone. And just wrapping up, we know through working with the thousands of the CPOs, and the CPOs not only have a good with building product, building teams, working with the board members, they also need a good system. And Dragonboat is the system help you to drive both the product and deliver business outcomes. So if you’re interested to check out more, go to dragonboat.io/cpo. Look forward to hearing from you and learn your journeys and then what you find out useful from today’s meeting. Thanks everyone.

Shelley Perry: Thanks everyone.

Dragonboat is the fastest growing product portfolio platform for outcome-focused teams to strategize, prioritize, plan and deliver products that drive business results. With Dragonboat, product teams can connect OKRs, customer insights, and product initiatives in one source of truth PPM platform. Sign up for a free trial or book a demo.

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Kenisha Liu

Kenisha Liu

Kenisha is the Marketing & Operations Coordinator at Dragonboat with a mission to empower responsive leaders and their teams to build better products faster. Prior to joining Dragonboat, Kenisha finished her undergraduate degree at UCLA in 2020, where she studied History and Cognitive Science. She was also a CSCAA All-American and Program Record-Holder on the UCLA swim team.
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