"Take Control of Your Desk" — Career Tips for ICs, Managers & Founders

When evaluating whether a startup has a promising trajectory:

• Pay attention to the investment cycle - who has invested, how much, who's leading the round, who's leading another round?
• Keep an eye out for movement in the C-Suite.
• Find out how the particular role you’re looking at fits into the company’s growth trajectory. For example, are they investing in cloud and security? Is there global expansion happening?
• You want to see if people have been growing in their careers at a company that’s at least a couple of years old.

• Ask about the one, three, and five-year future of the company.
• Probe their goals and what they're striving for. Do they talk about strategy and values, or are they executing as well?
• Where do they see their revenue growth coming from next year?
• Do they see the company going public?
• Ask about the career path for the role you're interviewing for.

• What initiatives were rolled out that changed the course of the product or the GTM strategy?
• What’s the most common reason people leave here and what’s the company doing to rectify it? 
• What are the most common reasons to promote people here?
• How would you break down what I’d spend an average day doing? 
• What percentage of your role tends to be more tactical versus more strategic?
• What metrics do I need to achieve to be able to be successful in my role?

• Don't limit yourself to roles that have already been created. Instead, see where your own skills sets, passions and goals overlap with opportunities.
• Keep in mind that the greatest opportunities for growth are at the intersection of the needs of the business and flexing your metaphorical muscles. You need to have data behind your proposal.
• When you make your case for taking on a new role, consider why they would say yes to your suggestion.

Hiring managers may mistakenly see job-hopping as a red flag. It could be that they job-hop because their role and career are growing rather than a lack of focus.

• However, be wary of people who are defensive when you question them about their changing jobs.
• See it as a red flag if they don't click with the manager at most of their jobs.

• Tell me about a time when you achieved success entirely on your own?
• What are you working on getting better at? Tell me about a time you’ve failed. 
• What motivates you?
• We love professionals who want to grow into their niche, and we also value those who want to climb the ranks. Which are you?

• Set the tone. Career growth is the report’s responsibility, not the manager’s. Let your hire know to take control of their own desk.
• Keep them challenged. Find out what motivates them and explain that uplevel doesn't always include promotion. It means growing skillsets and capabilities.
• Assign a rotating Devil's advocate. Assign a person to challenge the team to think with different frameworks.
• Create the culture within your team. Your job as the leader is to set the tone.

• Lead with authenticity. Refrain from startup cliches. "We’re the next big startup. We’re the next unicorn.” Instead, state what makes your company original.
• Career development often falls to the bottom for startups. However, you have to lay the foundation for future building blocks. Consider what employees have been in the same role for 18 months. They may not speak up until they finally quit.
• Invest in people who can take your career development plan to the next level.