15 Advice to Become A Better Entrepreneur

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Advice for Entrepreneurs: Have you ever thought about the steps you can take to improve your knowledge and expertise in order to become a better leader within your company, within your industry, or within your community?

A leader is someone who has a certain amount of expertise in whatever industry or niche they are in, and they are willing – and do – share their insights with those around them through writing, speaking and taking action.

What's truly exciting is how much we've learned about what our audience actually wants and needs, and how we can do our part to make the entire tech ecosystem stronger. This is what will drive us to talk to even more remarkable people, try new things, and tell great stories in 2016. Join us. Won't you?

1. Practice Radical Candor.

Kim Scott has built her career around creating bullshit-free zones where people love their work and working together. Now an acclaimed coach for Twitter, Shyp, and Qualtrics among others, she's made one simple tool the cornerstone of her teaching: Radical Candor. Basically, bosses need to tell their employees when they're screwing up, but it very rarely happens. Scott proposes a framework to make this easier:

If the vertical axis is caring personally and the horizontal axis is challenging directly, you want your feedback to fall in the upper right-hand quadrant. That’s where Radical Candor lives. It's the combination of caring a great deal and being willing to deliver difficult feedback, Scott said. “Radical candor is humble, it’s helpful, it’s immediate, it’s in person — in private if it’s criticism and in public if it’s praise — and it doesn’t personalize.”

    "I would argue that criticizing your employees when they screw up is not just your job, it's actually your moral obligation."

2. Use feedback like Slack.

Slack may go down in history for having the best go-to-market experience ever. Out of the gate it was crowned a unicorn and universally loved by its users. How did CEO Stewart Butterfield and his team accomplish this? For starters, they kept the product in beta for months to intimately understand their users, collect data and use it to fuel development. “We're fastidious about tagging all incoming messages across channels, collating, entering and retaining the data people share or send to us,” said Butterfield. This has allowed them to play to customers' priorities, optimizing the features they cared about most (i.e. search, synchronization and simple file sharing). On the quantitative side, it also gave the company a benchmark for success. They saw that once a team exchanged 2,000 messages on Slack, they'd be hooked. The company took the hint and baked new mechanics into the user experience to get customers to that golden 2,000 message mark. Spoiler alert: It worked.

3. Give away your Legos.

“The best metaphor I have for scaling a company is building one of those huge, complex towers out of Legos,” says Molly Graham, COO of Quip and former Facebook culture architect. Early on at a startup, everyone's excited and has so much to do. But when you start to grow, a funny thing happens: People get nervous. “As new roles get added, you go through this roller coaster of, ‘Wait, is that new person taking my job? What if they don’t do it the right way? What do I do now?’” The emotions you feel when new people are coming in and taking over pieces of your job — it’s not that different from how a kid feels when they have to share their Legos. At a scaling company, giving away responsibility — giving away that Lego tower you started building — is the only way to move on to building bigger and better things.

4. Make speed a habit.

“All else being equal, the fastest company in any market will win,” says Dave Girouard, CEO of Upstart, and former head of Google Enterprise Apps. “Speed is a defining characteristic — if not the defining characteristic — of the leader in virtually every industry you look at,” he said.

    "I believe that speed, like exercise and eating healthy, can be habitual."

The key takeaway: WHEN a decision is made is much more important than WHAT decision is made. You need to consistently begin every decision-making process by considering how much time and effort that choice is worth. There are decisions that deserve days of debate and analysis, but the vast majority aren’t worth more than 10 minutes. And, as you're executing, always ask this question: “Why can't this be done sooner?” Asking it methodically, reliably and habitually can have a profound impact on the speed of your organization. As Girouard put it: “A good plan violently executed now is better than a perfect plan next week.”

5. Heed the Series A Crunch.

Last year, First Round Partner Josh Kopelman observed this about raising Series A funding: The number of seed-funded companies recently quadrupled, and most of them set out to raise larger than average A rounds. This has unintentionally exacerbated a Series A Crunch — a rude awakening for companies that thought it would be easy to secure more capital. Kopelman's contention: This should fundamentally change the way early-stage founders think about raising money. For instance, some of the smartest founders he's worked with have raised larger seed rounds, buying themselves time to get more done before they pitch again. He also recommends forgoing party rounds to work only with investors who will roll up their sleeves to open doors, make intros, and concretely help with your next round. Then, once the money's in the bank, keep your burn rate low until you have product-market fit. “That's your best chance at building a big company that matters,” Kopelman said.

6. Your Team's Capacity = Your Executional Ability.

After co-founding and selling two startups to the likes of Oracle and Dropbox, Jessica McKellar has become one of tech's quickest rising engineering stars. In particular, she's known for her effective engineering management skills — not an easy feat considering how embedded she was in code for years. One thing she had to learn on the job and now espouses as gospel:

    "You need to level up everyone on your team all the time. Execution will follow."

If you're stepping into technical management, you need to get out of the codebase and make peace with feeling like you're not getting anything done. Because you are. “Keep this truth top of mind: If you can help the people on your team grow their individual capacity, you'll be able to get exponentially more done,” said McKellar. “This is all about matchmaking them with high-impact projects that align with their interests, the value they want to create, and how they want to grow. That's when motivation becomes organic.” The other key thing you can do? Maintain a balance between more experienced and less experienced engineers working together and regularly sharing knowledge. Build in opportunities to make these conversations truly bi-directional.

7. Forget GPA. Look for these candidate qualities.

The unwritten rules for how to hire are often plain wrong. With more candidates who “look good on paper” going on to flounder at startups, it’s time to rethink what traits actually make someone a great employee. As the co-founder and CEO of Koru, the business-training program designed for new job seekers, Kristen Hamilton works to place people in jobs where they’ll excel. She now has a crystal clear sense of the skills and traits that make people great performers. They are: grit, rigor, impact, teamwork, ownership, curiosity and polish — and she's developed interview questions and tactics to test for each trait. The takeaway for startups looking to hire great employees? Determine the qualities and competencies that are the most valuable for your company and thoughtfully plug away at a rubric for finding them. Don't be surprised if you see some overlap between yours and the seven Hamilton proposed.

8. Follow these steps for sustained growth.

Growth isn't just about user acquisition — in fact, that's just the first of four steps to real, meaningful expansion. Here's the progression every company should be looking for according to Meenal Balar, Facebook's early growth leader turned VP Marketing at Remind:

    Acquisition: How do you get people in the door?

    Activation: How do you get them to start using your product?

    Engagement: How do you keep them using the product and make them willing to come back?

    Virality: How do you turn engagement into people inviting others to join them using your product?

Each of these steps is multi-dimensional. When you break acquisition down, for instance, you need to think about product discovery, app installations, pricing considerations, etc. “Acquisition is largely about understanding how people discover and share, and mapping your product tactics to match the specific behavior you want to be driving,” said Balar. Similarly, activation requires extensive usability testing and investigation into user friction both inside and outside your product. Why do people come back a second or third time? Juice those attributes to retain even more new users. The more users you activate, the more you can engage — and that's when things really start to take off.

9. Run this 90-day plan for new managers.

After steering his way through multiple engineer-to-manager transitions, David Loftesness started shepherding other developers into their first leadership positions. Recently, he collected his wisdom on the subject into a 90-day plan for new engineering managers. The framework is segmented into three distinct stages: Own Your Education (Days 1-30), Find Your Rhythm (Days 31-60) and Assessing Yourself (Days 61-90). Loftesness has baked in checkpoints along the way to help rookie managers across all functional areas (not just engineering) gauge their appetite to commit to the career path, which is a much bigger deal (with bigger tradeoffs) than most people suspect. “This is an entirely new job. Don’t expect to just bolt-on some management work and call yourself a manager,” he says. “You now have people whose happiness and effectiveness at work rests largely on your shoulders. You’re responsible for the results but can’t do it all yourself.” Lean on Loftesness’ plan to get started.

10. Make performance a priority now, not later.

Since 2013, AltSchool CEO Max Ventilla has been working to reinvent education. To this cause, he brings years leading Google's personalization efforts, where he also saw one of the industry's most emulated and revered performance evaluation systems in action. This experience instilled him with a firm belief: That all companies can benefit from formal performance reviews at every stage. So Ventilla took on the herculean task of porting Google's “perf” system to the startup environment. His biggest lesson? Annual evaluations don't work for startups — you need to give and get constant feedback for smart iteration. “In a startup, things change so often that doing annual performance reviews seems just useless," he said. "We may have overcomplicated our process at AltSchool at the beginning, but we knew we’d be working at it for a while, and it was too important to do without. The critical thing is just to start.” With this attitude, Ventilla has presided over 10 performance cycles, has collected rigorous data on the experience, and has consistently shortened the time it takes so that the process keeps pace with the company's growth.

11. Replace policies with principles.

One of the best ways to beat bureaucracy at a startup is to get people to follow principles instead of polices, says Airbnb VP Engineering Mike Curtis. Every startup looking to dodge a fate dictated by increasing structure that inevitably slows you down can benefit from this tip. Here's an example from Airbnb:

    OLD POLICY: All expenses require pre-approval.

    NEW PRINCIPLE: If you would think twice about spending this much from your own account, gut-check it with your manager.

“I can't tell you how much pain in my life has come from expense reports,” Curtis said. Airbnb’s old policy was a cumbersome one: Charges big and small required approval before they could be submitted. So he tried replacing it with a principle, simple good judgment, using $500 as a rule of thumb for when to get a gut-check. The result? No increase in discretionary spending (but a whole lot of time saved). Principles create the social dynamics that keep everyone within the boundaries of what's right and good for the company.

    "The only way you can affect cultural change on an organization is through positive reinforcement and social pressure."

13. Sidestep leadership traps with this 15-minute daily practice.

As an executive coach for nearly two decades, Chris Holmberg has worked with leaders of tiny startups and multinational corporations alike. As he puts it, he's in the business of building mindsets that can handle anything. At the heart of his philosophy is one actionable exercise: Spend 15 minutes a day in reflection — true reflection, in a quiet space, with your inbox closed. He proposes a structure for how to spend this time too: “Look at the world through the lenses of the ‘It’ the ‘We’ and the ‘I.'” Then ask yourself these questions to methodically revisit your day:

    The It: Did you execute the stuff you had on your list at the start of the day? Did you do the things that were important and not just urgent?

    The We: Did you add value to the lives of the people you interacted with? Did they walk away with more knowledge, energy, goodwill, help, a better understanding? You want to make sure you communicated clearly in a way that added value for them and met goals for you.

    The I: How did you manage your own energy and mood? Self-care measures like working out, eating well, and sleeping enough are just as important as anything you do in the office. You can’t help others if you deplete yourself.

At the end of the week, Holmberg asks his clients to run the same exercise for an hour, only this time reflecting on the whole past week and looking ahead to the challenges and opportunities of the week ahead.

14. Constantly test new messages. Never stop.

Product management expert Gibson Biddle has led and coached brand creation for companies like Chegg, Sega and Mattel. But he arguably made the biggest impact at Netflix. In the early days, building the company’s brand meant not only finding ways to promote and position the “brand promise” of Netflix, but also introducing — and owning — language that was fundamental to an incredibly new business model (people hadn't heard of 'streaming' at first). Biddle helped the company achieve this exposure through constant calibration. “The reality is you're growing up as a company. You're getting smarter, better, faster. You're learning. At Netflix, we constantly tested the non-member landing page — the page whose job it is to convert prospects into customers — every two weeks, forever,” said Biddle. Alter your imagery, your language, your presentation, and A/B test until customers become more familiar with your brand. You'll always learn something you didn't know before.

15. Draw the owl.

Twilio Co-founder and CEO Jeff Lawson has become an outspoken teacher and student of company values. He’s brought granularity to a notoriously ambiguous topic by deconstructing these values into three stages: articulating, living and changing them. Twilio has nine values, precisely expressed. They are commandments and nearly every one begins with a verb. They contain five words or less, none of which are $10 words. Lawson has found that sparing, actionable language resonates better and feels more implementable. Perhaps the best example of a value that uses human, actionable words: “Draw the owl.” What originated as an internet meme spread through the company like wildfire in its early days. “It’s a great representation of our job. There is no instruction book and no one is going to tell us how to do our work,” said Lawson. “It’s now woven into our culture and reminds people that they are empowered to find answers for themselves."

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