The goal of professional development is to help our people accomplish their growth goals and, in doing so, improve your team's performance. Each member of your team should become clear around their own values, talents, skills, knowledge, and goals. Once they have that level of self-awareness, they should understand in detail what the next steps are for developing those traits and achieving their goals.

Your job is to guide them to the answer themselves. Then, once you understand where people are trying to go, you can make adjustments in their current role to move them in the right direction. This knowledge will also shape the feedback you're giving them.

You should have a distinct understanding of the future plans of everyone on your team (if you have direct reports) or work closely with the CEO to understand the growth trajectories across the company. Do they want to become a senior engineer, transition roles, or start their own business?

A great place to discuss this is in one-on-ones. We recommend having a professional development conversation at least once every quarter.

It's important to remember that Straddle is just a phase in people's lives. At some point everyone currently working at Straddle will leave. Indeed, at some point, Straddle won't exist! Our goal is to try and make it one of the best phases of people's lives, and set them up for whatever they want to do next.

Talking about Straddle as a phase is an important idea to convey before people share their career goals because most folks are used to keeping their true goals hidden lest they are looked upon as disloyal or having conflicting goals with the company. The relationship between leaders and team members is really a symbiotic one: the employee creates value for the company in exchange for growth opportunities that may or may not continue at the company.

Growth doesn't have to be at work

You may find that someone is quite happy in their current role and career. Perhaps they are focused on areas outside of work. That's totally fine. Don't force your definition of growth down their throats. If someone is doing great work for the company, and they're happy doing just that, let them do their thing.

Growth doesn't have to be an up-level progression

Growth is really learning new skills. You can grow by learning peripheral skills that interest you; e.g., as a back-end engineer, you can grow by learning distributed systems design (go deeper) or by learning front-end development or marketing (go broader).

These skills don't necessarily advance you to the next compensation level if the skills are not highly valued in your role. But you may still highly value the skills yourself because you want to found your own startup later. (This is also why being explicit about supporting someone's career goals up front is critical.)

The up-level progression is simply a recognition of your achievement of mastery in a set of skills highly valued in your current role and the impact that the new role will have.

Growth is not management

For whatever reason, our society drills into us that to have career growth, we need to go into management. This is absolutely not the case. If someone wants to go into management, great—but that's not a promotion, that's a career change.

Management requires a totally different skill set. If you have a report adamant on going into management, start discussing how to grow that skill set with them first. For a start, they should know this handbook back to front.

Career development at Straddle's stage

At Straddle, we don't yet have a formal leveling system. As we grow, we'll develop clearer career frameworks for each function. But our stage actually offers unique growth opportunities that larger companies can't provide.

Your role will evolve as we scale

At an early-stage startup, your role will naturally evolve in one of several directions:

If you're currently an IC leader without direct reports:

• You may build a team and transition more toward people management

• You may stay deep in the craft and become a senior IC as we hire more junior people

• You may expand your domain ownership as the company scales

If you already have direct reports:

• Your team will likely grow, requiring you to develop stronger management skills

• You may need to hire and develop other managers under you

• You may transition from doing + managing to primarily managing and leading

For everyone:

• The problems you're solving will get more complex as we scale

• Your scope of ownership will either go deeper or broader

• You'll develop skills that typically take years to build at larger companies

What growth looks like at our stage

Career growth at Straddle means:

Area	What it looks like
Expanding ownership	Taking on more responsibility within your domain or adjacent domains
Building leverage	Moving from individual execution to creating systems, processes, and eventually teams
Developing new skills	Learning skills you couldn't learn anywhere else (e.g., building from 0→1, wearing multiple hats, making high-impact decisions with limited data)
Increasing impact	Your decisions and work affecting larger portions of the company
Preparing for what's next	Whether that's scaling with Straddle or taking these skills to your next venture

The startup career trade-off

What you gain:

• Compressed learning timeline (1 year here = 3-5 years at a bigger company)

• Broad exposure across the business

• Direct impact on company trajectory

• Equity upside if we succeed

• Experience that positions you for senior roles elsewhere

What might be slower:

• Formal title progression (we're small, so there aren't many "levels" to climb)

• Compensation growth tied to traditional levels (though equity can make up for this)

• Specialization in a narrow craft (you're wearing multiple hats)

Having a discussion

Your professional development discussion should revolve around a 12-18 month plan and a longer vision. Ask people to come to their one-on-one prepared with answers to the following questions:

1. How would you describe your success in your current role?

2. What do you actually do that makes you as good as you are?

3. Which part of your current role do you enjoy most?

4. How does professional success intersect with personal happiness in the context of your current role? Do you think it's achievable? Why/why not?

5. What would be the perfect role for you?

6. What goals (inside and outside of work) do you have over the next 18 months?

7. What would you like to be doing five years from now?

8. Write down five to ten skills or competencies you think are required to get to this place, and then rate yourself on each of these on a scale of 1–10.

Since this is all prepared, you can do some thinking of your own prior to the meeting. The first thing to consider is self-awareness. Has the person listed all the skills and competencies required to get to where they want to be, and how does their competency rating compare to your impression of them?

If there's a lack of self-awareness, ask if they'd be interested in seeing your scores for them for each skill and competency. While this can be a tricky conversation, the alternative is doing them a disservice by not opening their eyes to any blind spots.

Lastly, ask for ideas on how to work on developing these areas. It's much better if the ideas come from them! Try to morph their role and incorporate growth in the areas they're interested in.

Mentorship

Mentors can be a powerful way of catalyzing personal growth. You should be a mentor to your team, but it's also helpful to look for additional mentors outside of the company.

We suggest working with your reports (if you have them) to set up support structures for them. Prompt your team to look in their network for people who can serve as mentors, and if you have anyone relevant in your network, offer an introduction.

Note: We don't currently have a formal external coaching program at Straddle, but we encourage everyone to seek out mentors and advisors in their network.

Taking responsibility for your own growth

Ultimately the ownership for career growth lies with the employee (not the manager or the company). While this idea can be counterintuitive for a lot of people, acknowledging it is the only path to true growth.

Leaders and the company are there to provide opportunities and shortcuts to growth. They have opportunities to apply in the real world some skill, or experts that have done it before to ask questions of. But they don't own growth; the employee owns it.

This means that an employee, not their manager, should be in the driver's seat about their own career. An employee should seek clarity around what they want to learn next and jointly work with their manager to seek out those things.

Unfortunately, it's all too common for folks to expect their manager to tell them what they should grow next. While it's important to explain what the company needs, it's just as important to bounce the question back: What do they want out of their life?