The Rhythm of the Fight: Why a Startup Needs “Cadence” to Succeed

Michael Wolfe
Aug 30, 2019 · 11 min read
Photo by Gabriel Barletta on Unsplash

“The execution is more important than the idea!”

“The best startups are execution machines!”

“Execute! Execute! Execute!”

Since you are reading this post, you are probably a startup founder or team member who reads lots of startup advice, which means you’ve seen many admonishments about how your startup must “execute.” It’s no surprise — although you might find a few exceptions, most successful startups execute extremely well, in addition to having a great idea (or pivoting to one).

But a piece of advice being true doesn’t always make it useful. Telling a startup team, “you need to execute!” is like telling a basketball team, “you need to score more points!” (thanks, coach!). Startups need help learning how to execute. Most founders have never managed a complex organization; many have never even worked at one. Startups are so difficult that just surviving the week can feel like a challenge, much less delivering “flawless execution” along the way.

Some founders interpret “execute” simply as, “work really hard.” Hard work is crucial (see a post I wrote about it), but great execution is not only about maximizing individual output — it’s about maximizing the entire team’s output, which requires very different skills than just managing oneself. Startups that don’t figure this out struggle once they grow beyond just a handful of employees.

No magic formula exists for great execution, but you can learn a great deal from successful startups. I’ve been fortunate to work at some great companies and advise many more via my work as an Advisor to Point Nine Capital. One attribute shared by the best executing companies I know is they have a great “cadence” for running their business. The cadence of a company is the set of habits and practices that it repeats on a set timeframe — daily, weekly, monthly, or quarterly. You can feel the energy of a strong cadence even during a brief visit to a well-run company. (Fred Wilson has called this “The Heartbeat” of the business).

You’ve probably read one of the numerous Medium posts on the routines and habits of successful people, often touting the benefits of waking up before dawn, meditating, exercising, and getting to “inbox zero.” Successful companies can be analyzed in much the same way: they have habits, routines, and disciplines which determine their success, just like successful people do.

It helps to start with a few principles that underlie great execution:

People. A startup wins by attracting the best people, keeping them happy, and letting them do their best work. Great people want meaning in their work, opportunities to learn, the possibility to advance, and minimal politics and hassle. Your company’s cadence should be designed to bond, motivate, and educate your team and to remove obstacles and frustration.

Learning. Any startup worth starting is building something that no one has ever built before, which means it starts out with more unknowns than knowns. It doesn’t know what product features will resonate, what sales motions will succeed, what marketing channels will perform, or how new hires will fit in. A great cadence optimizes for constantly gathering information, analyzing it, and making sure the team shares it with each other.

Agility. Learning only helps you if you adjust to account for what you’ve learned. This might mean adjustments to your product plan, your messaging, your competitive strategy, or your spending. The right cadence enables that agility: if you learn something important today, you want your entire company to be putting it into practice by tomorrow.

Productivity. You don’t want to spend time in endless meetings, but you also don’t want to waste a moment where people are working on the wrong things or are duplicating efforts. The ideal cadence brings teams together to check in regularly, like a huddle for a sports team, where they can make sure they are all working on the right things and identify places they can accelerate each other. The rest of the time they should have minimal distractions.

Discipline. Work is called “work” for a reason — it’s hard. A company is just a collection of individual people, and people procrastinate, deny bad news, avoid confrontation, and delay hard decisions. We all do it. Most self-help literature will tell you that the key to getting hard things done is not to wait for the occasional moments of inspiration, but instead to build hard things into your regular habits so that they happen routinely, much like booking a weekly boot camp class makes it more likely you’ll show up at the gym every Monday morning. The right cadence does this — it guarantees that hard discussions and decisions happen day in and day out. Cadence is relentless, but effective.

Everything your startup does should focus on solving these, including how you design your cadence.

Every company is different, and there is no recipe, but most successful companies I’ve been involved with, including my own, land on a cadence consisting of a regular set of weekly activities to keep the company moving as well as a few more strategic activities that happen on a longer timeframe, usually monthly or quarterly. This often looks something like:

Weekly executive team meetings. These are the meetings where the leaders of the company review progress, talk about tough issues, and make decisions. These meetings ensure that the team is always on the same page, has the most up to date information, and regularly debates and makes hard choices. The agenda covers the biggest projects or deals at the company, what key hires need to be made, what the latest learnings are, and what course corrections are needed. Monday morning is a great time for this meeting since it helps set the agenda for the rest of the week, and the discussions and decisions can cascade into the rest of that week’s cadence.

Weekly team meetings. Your company is trying to get certain things done. You have product teams trying to ship new features and improve user metrics, a marketing team trying to drive leads, and a sales team trying to close business. It’s almost always worth it to have each of these teams meet weekly and review status, share learnings, and make course corrections. For sales, this could be a weekly Friday forecast call, followed by a training session on a new topic. For the product teams, this could be a weekly project review meeting followed by a “deep dive” training topic. Some teams may even want to have a short, daily standup meeting, especially in engineering where daily scrums have proven to be an effective practice.

Regular one-on-ones. If management were an automobile, the one-on-one would be the steering wheel. One-on-ones are where the real work of a company gets done. They are the forum to give each other feedback, learn about new issues, brainstorm solutions, test messaging and strategies, coach and develop people, and build stronger relationships. Most managers schedule these weekly or, at most, bi-weekly, and never miss them. Lots has been written about how to do one-on-ones well (including, ahem, by me), but the key is to do them religiously and always make them a two-way discussion.

Weekly all-hands meeting. This is a chance for the entire company to get together, share progress for the week, celebrate successes, bemoan failures, train each other on important topics, and hang out. These are often done over Friday lunch or beers to make them more social and to celebrate the week’s successes. The all-hands meeting is not just a forum for managers to tell everyone else what is going on. They work best when they are community property, where different people take turns moderating the meeting, presenting topics, training each other, recognizing their peers, and celebrating wins.

Regular training events. You can never train people enough. You need to train engineers on your tech stack, your sales and marketing team on how to sell your product, and your customer success team on how to install and support it. For example, my company Gladly has invested in a great onboarding and orientation program for new employees, weekly training for the go-to-market teams, regular “deep dive” topics in weekly company and departmental meetings, and quarterly company “kickoffs” for team building and more training and role playing. You can almost never train people too much.

Quarterly or monthly planning. One of the advantages of being a small private company is that you do not get locked into an annual plan, with shareholders and boards of directors scrutinizing every deviation from a plan that was decided months ago. As a startup, you can adjust your plan any time you discover new information, which happens continuously. But you don’t want churn either, where the management team comes up with a new plan every week, whipsawing the company. The right planning cadence strikes a balance between agility and stability.

Effectively running a startup planning process could itself be a series of blog posts, but in summary, the key people at the company should regularly spend several hours together (preferably offsite) to have a discussion about what is working and not working, make decisions, adjust the plan, then use the new plan to run the company. There are multiple systems you can use, like OKRs or V2MOMs, but don’t get too hung up on the methodology: the benefits mostly come from just writing down a list of goals, who is responsible for each one, and then using them as the guidepost to drive activity across your company, like what projects to focus on, what people to hire, and how much money to spend. You should do this at least quarterly, although you might want to do them monthly if your startup is small and if your key metrics, like MRR, are on a monthly cycle.

Happy hours and team building events. It’s easy to forget to leave the office and have fun, especially when work gets busy and people get stressed, but you have to make time for them. Have a happy hour on a Friday afternoon. Take some time to go to the go-cart track or to play mini golf. Have an annual summer picnic that includes the whole family, including the kids and dogs. Let individual team members organize these, not the founders and executives. Your new hire who is two months out of college will invariably organize a rowdier happy hour than a busy and stressed out founder will.

On the face of it, this just looks like a bunch of meetings, which never inspired anyone, especially since many of your team members chose to work at a startup precisely to avoid the endless meetings and other trappings of big company culture. But it doesn’t have to be that way — resistance to meetings and planning comes from the assumption they’ll be a waste of time, but at a company that is executing well, they aren’t — they are where the business of the company gets done, and they leave people energized. When a startup is described as “executing really well,” it’s precisely skills like running great meetings, communicating well, giving hard feedback, and making hard decisions that is being referred to.

A few things your company can do to make your cadence effective are:

Connect the activities. Although each of these activities is valuable independently, great execution is an outcome of how the pieces of your cadence work together. For example:

  • In your monthly planning offsite, you make a decision to focus on a new vertical. You announce it during your Friday all-hands meeting. In team meetings and one-on-ones the following week, everyone discusses what it means for them and adjusts their work accordingly. Within a week, everyone is executing the new plan.
  • In one-on-ones with your staff, you learn that people are confused about your product roadmap. In your regular one-on-one with your head of product management, you share that feedback with her. In her next staff meeting, she brainstorms solutions with her team. They agree to revamp the roadmap training presentation, which they present at the next Friday’s all-hands meeting.
  • At a trade show, one of your marketing staff sees your competitor’s demo and learns how that competitor is positioning against you. They alert the product marketing team, who brainstorm solutions in their weekly staff meeting. At the next week’s sales training meeting, they retrain the sales team on new traps and blocks against that competitor.
  • In the sales forecast call, you learn that several prospects are being asked for a product feature that, using an API you already have, the product can already do. The next week the product teams work on documentation and a demo for that feature and then train the sales team on it during the next week’s sales training.

Include everyone. If the executives are doing the talking and the rest of the team is passively receiving information, you‘re doing it wrong. Anyone at any level of the company can moderate a meeting, give a training presentation, organize a team-building event, or take on a process improvement project. This is how they learn to become leaders themselves. You want the whole team to participate in driving your execution. If people are sitting around wondering what the management team wants, that’s a sign of dysfunction.

Be transparent. A culture of transparency motivates people, helps them develop their careers, builds trust, and increases agility. Much has been written about transparency (see my piece, The See-Through Startup) but the summary is that you want everyone to have immediate access to the information they need to do their jobs and to give context and motivation for their work. Have your discussions in public Slack groups, not in private groups or email threads. Keep your documents on a shared public file share, like in Google Drive or a collaboration tool like Notion. Take notes during meetings, and share them with the company. Use the Friday all-hands meetings to talk about learnings and decisions with time for Q&A, where no topics is off limits.

Stay consistent. When things get busy, it’s tempting to start skipping meetings, one-on-ones, planning, and team building in favor of spending more time at your desk working. Don’t. The times you are busiest are exactly when it’s most urgent to stay in touch with people to make sure the team is doing everything it can to make tough deadlines and make hard tradeoffs. A sports team would not stop practicing once it’s made the playoffs, so don’t start skipping the things needed to run your company since you feel “too busy.” You’ll save time, get more done, and have a happier team if you commit to a cadence that‘s even more vital during busy times.

Never be satisfied. For everything your company does (meetings, planning, one-on-ones, team building events, training events), get feedback from team members on what’s working and isn’t, solicit ideas to make them better, and relentlessly improve them. Don’t throw up your hands and stop just because you have a few meetings that are duds. Get feedback, try different things, and keep improving. I’ve been at companies where it’s taken a year to settle on exactly the right agenda for a key staff meeting or to figure how best to onboard new employees. It takes time.

Good luck!

Note: this post was largely derived from a I talk I gave called, “The Startup Operating System” at the annual Point Nine Founder Summit.

Point Nine Land

Thoughts about SaaS, B2B marketplaces, venture capital, and occasional sneak peeks into P9’s kitchen

Point Nine Land

P9 is an early-stage VC focused on B2B SaaS and marketplaces. Point Nine Land is where the P9 team (and sometimes members of the wider P9 Family) share their thoughts on SaaS, marketplaces, startups, VC, and more.

Michael Wolfe

Written by

Co-founder, Gladly. Advisor at Point Nine Capital. Five startups. Endurance athlete, SF dweller. Quora addict. Fanboy.

Point Nine Land

P9 is an early-stage VC focused on B2B SaaS and marketplaces. Point Nine Land is where the P9 team (and sometimes members of the wider P9 Family) share their thoughts on SaaS, marketplaces, startups, VC, and more.