Advice for startup employees

Working in an early-stage startup is different to working for a larger company: while many people fail to get anywhere in startups, others skip years or decades of career milestones. Granted, every startup is different. However, I have noticed a few common patterns across many startups that describe the most successful talent.

Understand what you’re here for.

Is your job to get things done, or is your job to create an outcome? This is crucial to understand first and foremost because it determines the mindset you should bring to your role.

If your job is to get things done, then you should set your goals and ways of working based on this. Deeply understand the priorities (e.g., which tasks need to be done instantly, which tasks can wait). Don’t get too emotionally attached to the outcomes of your work as this will lead to unnecessary stress.

If your job is to achieve an outcome, your first priority is to prove yourself enough to gain as much power as you will need in order to control the things that you need to control to achieve this outcome. For example, if, as a product manager, the biggest obstacle to achieving your outcome is actually the ways of working of your customer success team, you need the power to heavily influence how they work. This is a difficult job, but it will be incredibly fulfilling if you succeed.

Understand what you can actually control.

I recommend directly asking during the interview process, or at least once you start, what you’re actually allowed to do. Are you allowed to ruffle feathers? If so, where? Within your team? With specific other teams? Or anywhere in the company? Stick to affecting change within this defined sphere of influence until you get the blessing to branch out (assuming you want or need to).

Over-communicate.

Send a weekly update to your manager and your team highlighting wins, losses, things that are top of mind. People in startups often fail because leaders are unaware of what they are doing. Leaders only notice the really great things, and the really bad things. If you don’t communicate all of the other wins, they’ll go unnoticed. You could even do it daily. Don’t expect a response, though. Don’t create unnecessary work for people by doing this.

Take control of your own career development

But exercise a reasonable amount of patience. Early-stage companies struggle to find time for real professional development. Don’t expect anyone to do this for you. Take control. If you want feedback, ask for it. Be specific when asking for it. General “what feedback do you have for me” is unhelpful. Ask how you went on a certain project, or for feedback on a specific attribute. If you need more money, ask for it. Be specific about what you actually want. Don’t waste time on politics or negotiations. Start with your non-negotiables. If you want a six-month review, ask for it. But don’t be disappointed if it doesn’t happen until month 7 or 8. This is the norm given how poorly resourced startups are. If you don’t like this, you should work at a bigger company.

Rise above the gossip, politics, and bullshit.

Small companies fester gossip. This is inevitable because every single person on the team is competing for the same attention, influence, and resources, and everyone has an opinion on everything. Leaders notice who gets stuck in the mud, and who stays out of it. It’s rarely obvious how much this is affecting the opportunities that are given to you, your prospects at the company, and your reputation in the market.

Believe in the product, company, and mission.

Delusions of grandeur power startups. The best startup employees find a way to believe as strongly as the founders. The reality is: you have no idea if anything you’re doing is actually going to work long term. The things you’re optimistic about will fail. The things you are cynical about will succeed. Your chances of success are far greater if you believe, though. Fake it until it’s true.

Operate with absolute integrity in the market.

Never take an interview with a direct competitor and divulge sensitive information. Avoid all conflicts of interest. This is another one of those things that people are unaware of how much it is affecting their career within and without their current company. Just because it’s legal or technically permissible doesn’t mean it is fair game or good for your career.

Maximise salary and equity 1-2 years into your journey.

People underrate how much leverage they’ll have after a year or two into their role. As a candidate, your experience is valuable, but rarely crucial. As a tenured employee, if you’re talented, you’ll seem completely irreplaceable due to your contextual experience. This is the best time to negotiate on comp. This may seem risky, as your comp may not come to fruition, but you should only work in an early-stage company if you truly back yourself and if you are happy to take big risks.

Reduce cognitive load for your team, and especially your leaders.

Every time you ask for direction, you distract your coworker from another unrelated task. Make it as easy as possible for them to help you.

• Put questions and requests at the top of your message/email, with additional context and notes second.
• Make it extremely clear when something is an actionable request and not just a comment.
• Provide all necessary context in your requests. Link to the Slack message you mentioned, the deal in HubSpot, the ticket in Zendesk, the ad creative in Facebook Ad Library, the page in Notion. If your manager needs to know certain things about a prospect to approve a deal discount, include those details in your request. Remind them what you discussed last time you met.
• Make the decision yourself, but offer your leader a chance to overrule you. e.g., “I’ll email the vendor tomorrow morning with xyz price. Let me know if you disagree and we can adjust approach”.
• Write short, concise, to the point emails, documents, and messages.
• Only demand an immediate response if it’s actually necessary.
• Adopt the communication medium of the business. Some companies are Notion companies. Some use slide decks. Others are all-in on digital whiteboards. However your team communicates, take that on. Going against the grain in this regard is rarely productive.
• Communicate and confirm priorities to eliminate ambiguity. Tell your leaders and team what you’re prioritising for the day or week, tell them what you’re consciously neglecting, and let them object if they disagree.
• Take every opportunity to advertise yourself and your work in front of the company. Speak at All Hands, no matter how bad you are at it. Ask the CEO if you can give them a quick demo of something you just built. Share videos of your product demos in #general/#company-wide on Slack. Dial into All Hands when you’re sick or on holidays, at least occasionally.
• Don’t complain. Pointing out problems is fine, whinging will make working with you feel like a chore, though. Practice extreme stoicism in the workplace.