Founders have always faced an intense pressure to have it all — a singular, world-changing vision for a new product, the unique charisma to impress potential investors and rally employees, and the business acumen to navigate through all stages of company growth.
In the midst of the COVID-19 crisis and ensuing economic turmoil, these dynamics are only heightened, upending carefully-laid plans and adding more to the load on founders' shoulders. This burden is made all the more heavy by a founder's natural inclination to retreat and turn inward in the face of a crisis. Whether a startup is in an industry that’s accelerating due to off-the-charts demand or one that’s stalling out due to a severe crunch, this feeling that it falls on founders to “figure it out” and formulate a winning game plan is intensifying at a rapid clip.
But as we assembled our founder field guide for navigating this crisis last month — drawing on countless hours of working sessions with First Round-backed entrepreneurs and the interviews we conducted with over a dozen recession-era founders and CEOs — one theme came up again and again: Founders shouldn’t feel that they have to go it alone. An abundance of support and high-quality advice can make all the difference in times like these, which means getting the most out of your existing network of advisors and investors has never been more important.
Of course, all the usual disclaimers apply here. Even founders who have gone through the ringer of past recessions are quick to point out that we’re currently living in singular circumstances. There’s no tried-and-true playbook for the [insert-your-preferred-adjective here] situation founders are facing right now. Advice is by no means a silver bullet. And as we’ve previously noted, we’re steadfast believers that the best advice often doesn’t always come top-down from the usual suspects, but rather bottom-up from the wisdom of fellow entrepreneurs.
But even with these caveats, what remains true is that no one person — founder, investor, advisor or otherwise — has all the answers right now. An ability to effectively seek and hear out different perspectives can make a meaningful difference as founders try to find their bearings and chart a new course for their startup. In other words, the mere act of collecting and evaluating advice, even if it’s ultimately discarded, can be the compass that guides founders through this storm.
But that’s no easy feat. Right now, we’re hearing from founders who feel like they’re drowning in a sea of well-intentioned but overwhelming and often contradictory guidance: Make drastic cuts or don’t cut at all, pivot quickly or stay the course and wait it out. A group of peer CEOs or operators-turned-advisors might suggest one path, while traditional investors or board members may push for more dramatic shifts in strategy.
Which brings us to the subject we’re tackling today on the Review: Advice on how to get advice. It might seem like a bit of a meta topic, but nonetheless it strikes us as one that's particularly useful to cover. To assemble today’s piece, we’ve gone back through our extensive archives to surface the best tactics for shoring up your sounding board so it’s more solid than ever. Critically, this isn’t advice on picking advisors — but on how founders can maximize the expertise of advisors they’ve already assembled, hold up their ends of the bargain as advisees, and cut through all the counsel they’re receiving to hone in on the most crucial insights.
What follows are the key lessons on how to make the most out of your advisors that we've published on the Review over the years. We hope they come in handy for you, especially now, when the need to lean on each other has never been more important.
1. Be prepared to spar, benchmark and direct your own learning.
In the midst of so much uncertainty and shifting priorities, your advisors (especially investors) are likely more involved than ever in the decisions you’re making as a founder. But without the right structure in place, this well-intentioned advice can simply contribute to more noise that complicates your decision-making process. First Round partner Phin Barnes has always felt that there’s opportunity being left on the table here in these founder-advisor relationships. Previously on the Review, he shared a collection of tactics on how to get more out of your advisors — we’ll highlight a few of his tips here on how to narrow the focus and extract the best insights.
Meet your new sparring partner.
When you first started a relationship with your investor or advisor, perhaps you had a formal discussion about what was expected of each party. More likely than not, this was a much more informal conversation. Now that you might be leaning on them more than ever, there's an opportunity to define — or redefine — the relationship, even with advisors you’ve had for years, and the onus is on you as the advisee to do so.
Here’s what Barnes has seen to be most effective: “Define your relationship this way: You’ll tell them what you’re thinking or planning to do, and their job is to back you into a corner and make you fight your way out,” he says. He defines this role as that of a sparring partner, forcing you as the founder to defend and explain your positions.
The entrepreneur often already has the best answer to a problem. A good advisor will bring it out by forcing them to walk through the problem again and again.
With this sparring dynamic, you’re able to practice defending your positions, and hone and strengthen your own arguments, while the advisor brings their history and experience to the table in a more complementary way. As a founder, you can decide what questions are relevant to your company in the present, when to listen and when not to. “The marginal change that occurs when a founder has to defend or explain their position is where the real value is created,” Barnes says.
So how do you identify those impactful areas where you could most use your sparring partner? “If you’re a founder, think about your job day-to-day leading your company. You’re probably making a bunch of decisions fairly quickly or effortlessly, but where are you hesitating?” Barnes says. “When I was running my own startup, I knew when I had a blind spot or when I wasn’t certain because I just felt different — less confident, more patient even. I would find myself waiting on things, trying to collect more information.”
Wherever you find yourself balking, that’s where you should engage your advisors. Even if you don’t know it yet, it means you need help.
As a quick aside, this point from Barnes on the dangers of hesitation reminded us of something we recently heard from his fellow First Round partner, Josh Kopelman, as we worked to put together our field guide to crowdsource advice for founders facing this crisis:
“When the action you need to take is painful, like austerity measures, there’s a cognitive bias toward delaying until you’re very certain the actions are necessary. The issue is that in a case where the probability of the worst-case outcome realizing increases with time, by the time you are certain about the need to act, it may be too late. Doing nothing is a decision. It’s the same as actively choosing to stay on the same path. And most founders don’t realize that. If the winds are changing, a smart sailor will adjust their sails.”
So if you find yourself with this instinct to hesitate on a big decision, recognize your potential bias toward not acting and remind yourself that it’s an area that you could likely put a sparring partner to work.
Benchmark yourself as an advisee and avoid the student-teacher dynamic.
Another strategy to maximize an advisor’s contributions is to benchmark yourself as an advisee, Barnes says. “A founder once asked me: ‘Across all the people you work with, am I getting more help out of you than average or less?’ They were basically assessing the quality of our engagement. When I said they were about average, their next question was, ‘How can I get more?’”
Barnes was really impressed with this tactic. He had no idea how much this particular founder wanted to be in touch on a more regular cadence, but was happy to offer more once he knew. Now more than ever, this is a key question to put to your advisors. This will help you assess if you’re really maximizing these relationships, or if there’s more that they have to offer that you’ve yet to tap into.
Another key takeaway is that as a founder, you need to take charge of all of your advisory relationships. Even if these people are more knowledgeable in certain areas, there shouldn’t be a student-teacher dynamic. “You’re not just showing up and sitting in class with your startup’s advisors,” Barnes says. “This needs to be 100% self-directed learning. Manage that relationship. Own it.”
Your advisors’ job is to deliver their best to you, but your job is to drive things so you get the most out of them.
Read more from First Round partner Phin Barnes about getting the most of of your startups’ advisors.
2. Master the art of contextualizing your requests.
“I don’t often seek advice. I ask for candid feedback, additional information, more data — that’s a whole different story. In the rare moments when I ask for advice, I look for someone who can help me think about a problem in a way that I haven’t considered. Only when I’m truly looking for a change do I consider soliciting advice.”
As co-founder of multiple SaaS startups including KISSmetrics, Crazy Egg and most recently FYI, Hiten Shah has been in the position of asking for guidance countless times in his entrepreneurial career. He’s also been an angel investor and advisor to dozens of companies, where he’s in the position of dishing out plenty of advice. Along the way, he’s observed many of the common pitfalls that cause well-intentioned advice to have limited usefulness, or how advisees miss crucial opportunities to further tap into their advisor’s wisdom.
It’s Shah’s belief that powerful, company-altering advice is only as good as the question that preceded it. “Here’s what I know: in most cases where advice has its greatest impact, the work begins with the advice seeker. If that’s you, take time to investigate where you need help in your business before asking for it. Don’t settle and immediately ask others about their past experiences. Dig into where you need to grow next. Start with your business fundamentals. That sounds basic, but I’m constantly surprised how many people forget it.”
When asking for advice, you should be on the verge of acting, but may not know how. At that point, it should be less about your motivations to act, but your method of doing so.
Shah has found that most people ask him for advice in a way that starts by asking what he did in the past. But these questions have limited value, because no two companies are exactly alike. Instead, start by sharing your situation. Your advisor will naturally bring their personal experience into the answer, but by framing the question this way you avoid speaking entirely about what has worked for other companies versus what is best for your particular circumstances.
Here’s a few examples of this in practice.
These are common questions that Shah receives from those seeking his counsel:
When you started KISSmetrics how did you start your blog?
When you hired your first salesperson where did you find them?
When you raised your first round of funding how did you do it?
This would have been a better line of inquiry to start:
I’m figuring out how to do marketing for my business. What should I be thinking about?
I’m starting a sales team and trying to hire the first person. How should I approach it?
I’m thinking about raising money. Where should I start?
This would have been their best line of inquiry to start:
I’m figuring out how to do marketing for my business. Here’s what we’ve tried out and these are the few tests we’ve found to work for us. What should I be thinking about next?
I’m starting a sales team and trying to hire the first person. Here is who our target customer is, our average revenue per customer and what our sales process looks like. How should I approach it next?
I’m thinking about raising money. I raised my seed six months ago led by this firm, it seems the profile of this partner is the best fit and these are the reasons we’re raising a round right now. What should I do next?
There’s a few key differences between the first set of questions that Shah receives and the rewritten version. The top takeaways are:
Favor questions with verbs in the present participle versus those in the past tense. Using “ing” verbs roots the advice giver and receiver in what’s currently in motion — and can be acted upon. Asking about what either party did should be brief as context, secondary and teased out through the conversation if necessary.
Root the question in data. The difference between the good and best line of advice-seeking is pithily providing a spread of data points between which the advice giver can draw the lines. This data rapidly signals to the best advice-givers where you are in the process, the questions you’ve likely asked — and haven’t asked — and your understanding of where you are. It also accelerates the conversation by cutting the pretense and quickly placing both parties on the same page.
Ask what you should do next. Any good advice should lead directly to action rather than focusing on the past. Asking for counsel on what you should do next transmits to the advice giver that you are ready to take immediate and concrete action.
Read more of Shah’s tips for advice seekers and advice givers.
3. Maximize strong advisor relationships — and bolster those that are lacking.
As a founder, you’re used to measuring the success of your business with quantitative numbers, from revenue to customer retention to pipeline. However, advisory relationships have limited metrics to define success and rather feedback tends to be qualitative. Amy Chang, founder of Accompany (a networking startup acquired by Cisco) and current EVP and GM at Cisco Collaboration, has amassed dozens of advisors over the years and similarly struggled with measuring the effectiveness of these relationships.
Over time, she developed a simple formula to pulsecheck the impact of her advisor network. She uses two key indicators to evaluate if the advisor relationship is functioning well:
1. Whether or not an advisor is responsive to the company’s needs on a regular basis.
2. Whether you feel like you “quantum-leap” your knowledge on a topic whenever you speak to the person.
Here’s a good indication of a great advisor: Every time you walk away or hang up the phone, you feel like you need to spend more time with them.
Not there yet with some of your advisors? Using that framework, Chang offers a few suggestions for turbo-charging your output.
Know what it means to follow up.
This is the most important thing you can do. Whatever advice someone gives you, tell them how it was considered, acted on or applied, and what happened as a result. Your advisors care deeply about giving advice or creating connections that make an impact for your business and want to know their time is being well spent. Reminding them that their guidance had an impact on you and your business is a critical best practice. However, one of the challenging pieces of follow-up is staying organized and keeping track of where advisors have been helpful — especially when you spread this across multiple advisors, investors and mentors.
Chang has solved this problem by keeping a running document of one-liner ideas contributed by advisors and makes a point of revisiting every six months so she can follow up with how that idea generated impact. (Editor’s note: Given how much is changing right now in our current climate, you may want to shorten this time frame for follow-ups.) This could mean following up regarding a piece of feedback that impacted the product, a customer connection that proved fruitful or a tactic for managing founder stress. Start keeping your own document that lists pieces of advice across all of your advisors, and set a calendar reminder to revisit this list on a regular basis so you can identify areas that warrant a follow-up with the key results from that piece of feedback.
Bring them into the team.
As the founder, you are likely the primary person interfacing with your company’s investors and advisors. Giving your advisors the opportunity to get to know the larger team is an opportunity to further flesh out their picture of the business. Don’t keep the relationship unilateral — invite an advisor to speak informally with your team and introduce them to everyone. Host a (virtual) dinner for them with the team and set a topic around a big question the company is wrestling with. It will cut out the small talk. If an advisor seems suited to it, you can also ask them to mentor one of your star players. It will make them feel even more helpful and necessary to your company’s success, plus give them a different perspective on the challenges facing the business.
Don’t hold back.
You’re only hurting yourself if you’re not 100% vulnerable and transparent with your closest advisors. While this certainly means being honest with where the business stands and the numbers you’re seeing, this also includes being honest about your emotions. Seasoned professionals make the best advisors because — like therapists — they’ve seen (almost) everything. They’ve seen founders that are upset, angry, sad, scared, and they’re equipped to help you deal with it. “Give your close advisors a chance to help you with not just the issue your company is facing, but your psychology around the issue too,” says Chang. “It’s an incredible relief.”
Read more of Chang’s advice for building strong relationships with your advisors.
4. Carve out time to spotlight what’s valuable.
Like all successful relationships, advising is a two-way street. As a founder seeking advice from your mentors, investors and advisors, it’s crucial to make sure that you are demonstrating appreciation for those that help you tackle the twists and turns of running a startup. However, right now things are so chaotic that taking a beat to pick your head up and say “thank you” to those that have provided game-changing advice can get lost in the midst of other to-do list items.
Patrick Ewers, an early LinkedIn director and relationship-building expert, agrees that the concept may sound remarkably simple, but he rarely sees people taking advantage of it. When we spoke to Ewers for the Review a few years ago, he introduced us to the idea of “value payloads.”
“I love the term value payload because it sounds so tangible,” says Ewers. “Value payloads are anything you provide to people that could help them. They could be introductions to people they want to meet, articles about a problem they are trying to solve, a note saying you saw their work and sent it to someone else. Most of the time it requires sending one email, which is easy to make a habit.”
The easiest value payload — it literally costs you nothing — is the emotion-based value payload.
“All an emotion-based value payload requires is giving people positive feedback in the moment. Many people have this odd tendency to be overly careful when giving out compliments or positive feedback. How often is someone talking in a meeting and you think, wow that was really smart, but you never say it out loud?” he says. These small-but-mighty tweaks can make a big impact in your relationships with your advisors — both in the midst of COVID-19, when you’re relying on their advice more than ever, and beyond.
He continues that as granular as these tasks are, he rarely sees them put into action. It starts with building a habit. What does this look like in the context of boosting your relationships with your advisor and mentor network? At first, you may have to force yourself to do it. Ewers recommends sending at least one note to someone in your network every day. Whether it be a quick email to one of your mentors to send over an article you found interesting, or a message to one of your investors to thank them for their advice on a particularly thorny issue, building this habit of gratitude is important to ensure these small-but-mighty relationship-building tactics don’t slip through the cracks.
Ewers understands that for almost all of us, asking for help can be challenging and even intimidating. Often, you might be worried that you’ll leave a negative impression that you’re weak or exploiting the connection. Founders in particular might worry that investors will lose confidence in the founder’s ability to lead. But Ewers sees asking for help as tying back to the idea of value payloads — and it’s something you give to others by asking for their help. “People love being asked for help. It’s easy to forget that,” he says. “When you ask for help, you’re telling someone they are an expert. You’re telling them they’re knowledgeable or influential in a space that is important to you.”
Read more about Ewer’s belief in the power of value payloads.
5. Treat all of your advisors like mentors — and follow these commandments.
Whitnie Low Narcisse has led First Round’s mentorship program since 2016 and observed nearly a thousand mentor-mentee matches. In talking to the most successful mentors, she’s developed a list of commandments for how mentors and mentees alike can get the most out of this crucial relationship, which is very relevant to our theme of maximizing the power of your advisors.
Whether you’re looking to tap into the well of knowledge of your informal mentors, or maximize your relationships with your investors and equity advisors, these tips are guideposts for keeping each touchpoint structured and productive.
Show up prepared with questions.
Every mentor Narcisse spoke to said they loved when mentees sent what they wanted to discuss in the meeting in advance. By sharing questions, problems or discussion topics ahead of time, this allows advisors to prepare and come armed with what they’d like to contribute or ask clarifying questions prior to the meeting. Successful advisors highly encouraged advisees to treat meetings the way they would 1:1s with their boss, where you set the agenda and own the content of the meeting.
This advice feels especially pragmatic now, when you’re likely facing a series of fires to put out. Leaning on the power of structure and focus helps you pull out more powerful advice from every meeting.
A good rule of thumb is to come with one topic you definitely want to address and a short list of three to five questions that will get them the clarity they need on that topic. This exercise in planning makes sure time is used wisely. When communicating this to advisors, consider framing your questions as: “Here’s what I’ve been wrestling with since we last met, can you please think about how you’ve approached this kind of thing in the past?” That way, advisors have time to think back on their history and pull out the most instructive examples and tactics.
Particularly when working with your formal advisors — investors and board members — sending out materials in advance is crucial. “You can always depart from whatever agenda has been set if something more relevant or pressing pops up, but the fact that it was created gets everyone thinking and aware of what the big issues are,” says a mentor that Narcisse interviewed.
Generally speaking, those who put a lot in are able to get a lot out.
Don’t boil the ocean in every meeting.
One of the hazards is that there can be far too much to discuss with your advisors, particularly in times like these when there is so much change happening on a daily basis. Very few founders only have one major challenge or problem on their plate. It can be tempting to unpack everything that’s going on lately. This will only limit how deep your conversation can go on the issues that matter most. Be really intentional about picking the two to three questions you really want to solve in the space of an hour.
“Try not to veer into big, conceptual thinking or conversation,” says Narcisse. “If you take on something huge like how to manage your team effectively, it’s easy for your time to run out without actually tackling the practical stuff that’s coming up the next week or month. Try to keep things really tied to the decisions that need to get made, or the solutions that need to be found.”
One preventative measure to try: If a meeting agenda is too jam-packed, or if things start with either party listing too many concerns, call a timeout and rewrite that agenda. Advisor and advisee should take five minutes to co-create a more realistic and focused punch list. Don’t try to do too much, be ruthless in paring topics down. You can always schedule a follow-up meeting to discuss the topics with your advisors or investors that you weren’t able to tackle, but by hyper-focusing on one thing at a time, you avoid just dipping your toe into each agenda item rather than digging deep and coming up with concrete solutions.
Read about the other seven commandments in Narcisse’s 10 full Review article.
6. Keep imposter syndrome at bay.
The founder’s perch can be lonely, especially in choppy waters. There are countless company-altering decisions that are resting on your shoulders. You feel the weight of your employees, investors and advisors trusting you to make the right decisions, often with imperfect information. Asking for help from one of your advisors or investors can feel like you’re admitting that you don’t know something you’re supposed to. Yet, a common theme across these tips for building deeper relationships with your advisors and investors is about getting candid and vulnerable. So how do you get over the hump of imposter syndrome so you can really ask for help — and feel prepared to receive it?
Three-time founder, investor and advisor Jeff Wald has become much more comfortable talking about vulnerability and failure, but it was a long road to get there. He’s the first to admit he avoided getting vulnerable about all the ups and downs of his career, which included companies folding, legal disputes with co-founders and twists and turns of the acquisition process. (Read more about his journey here.)
Over time, he’s become much more comfortable with discussing failures and tackling this idea that you need to have all the answers as a founder head-on. Now, as an investor and advisor, he shares the same mentality with the founders he works with.
At the time of his company Spinback’s woes, Wald knew he wasn’t the only founder coping with a defeat. But swimming in the despair of losing his first company, he felt isolated and alone. “Looking back, here’s what I needed to hear: ‘Do you think you’re the only person who’s been down this road? You’re not. Sorry, you’re not special,’” he says. “And I’ll tell that to founders I advise and invest in now. You failed. You’re going to fail again. It sucks. I'm not pretending it doesn't. But once you’ve had your time to wallow, take your lumps, dust yourself off and get back out there. Your investors, advisors, mentors and friends will be there to help,” says Wald.
Once you’re honest with yourself that having past failures isn’t an indictment, you’re able to have more honest conversations with your investors and advisors about where you need help now. It’s about being vulnerable enough to shed the veneer of having all the answers — and recognizing that your investors won’t expect you to — especially given we’re all currently operating in rare circumstances. Especially now, your advisors understand that you are facing numerous unforeseen challenges, but they can’t help you navigate these choppy waters without awareness of the full picture. It’s also important to remember that your advisors are also likely feeling some of the same imposter syndrome challenges. Even investors that have steered companies through multiple economic recessions have never faced a global pandemic on the magnitude of COVID-19.
In order to start feeling more comfortable with transparency, it can help to talk to other startup leaders — your peers — who can discuss their own failures and feelings of not quite measuring up. Managing imposter syndrome is a moving target and something that you’ll need to continue to assess. No one knows that feeling better than your fellow entrepreneurs.
Don’t just read about industry deities — take inspiration from the founders that surround you. You need to hear the stories from the trenches that will help keep you going.
Read more about Wald’s lessons in the power of true vulnerability.