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4 Steps to Create a Strong Leadership Culture in a Startup Environment

By Stephani Martin

New managers need more than technical know-how to be effective in their roles. They must develop a wide range of soft skills, ranging from effective communication to time management. A strong leadership culture can help them meet these challenges by offering guidance, training, and support. Even in a startup environment, it’s crucial that company leaders pause to make this investment in their new managers.

Throughout my career in People Ops, I’ve worked alongside executives in the startup space to cultivate strong leadership cultures. The majority of startups are charging forward at break-neck speed, growing faster than their resources can match. That’s why even small companies must develop sustainable leadership practices — notably, to support first-time managers who have been promoted from within. At Affinity, I have had the unique opportunity to watch a small company build a leadership culture from the ground up. I learned that fast-paced growth must be matched by leadership development in order to remain stable.

Here are a few takeaways I’ve gleaned from my time in the startup space.

Wait until the timing is right

Before a startup begins crafting its leadership development training program, they must be sure the timing is right. Typically, new companies are busy building a viable product and finding product-market fit. Understandably, developing a management career path may not be a focus at the offset. In some cases, a middle management layer may even seem excessive — it may be ideal to grow with a lean team for as long as it's sustainable.

However, at a certain point in a startup’s lifecycle, operating as a flat organization will no longer be feasible. At this stage, teams will benefit from having a dedicated leader for functional teams (e.g. engineering, customer success, etc.). The tipping point is different for each company, but here are some early signs that it’s time to create this new structure:

  • A department lead, typically an early hire, has too many direct reports.
  • The founders are no longer able to give attention to a growing function or department.
  • A functional area starts accelerating its growth (or on the contrary, decelerates due to lack of focused attention).
  • Processes start to break down or mistakes are made in key areas of output.

This isn’t an exhaustive list and, of course, each organization is unique, but these four patterns are among those I most commonly see at growing startups.

Design the middle-management career path

If you think you’re ready to establish that middle management level, how do you choose managers? Well, you won’t know unless you ask! The choice to embark down the management career path should be made by the employee. Too often a highly productive employee is asked to be a manager because they’re the subject matter expert. However, becoming a leader is an exercise in self-development — it requires considerable time and energy. If they are not fully invested, even the best employee may flounder.

  • Discuss personal aspirations with each direct report. Through these conversations, you will learn that no two people share the same vision for their career. Some may want to become subject matter experts, while others really want to manage a team. 
  • Create custom-tailored opportunities. The lifespan of every startup can be viewed as an arc, which overlaps with the arc of its employees’ careers. Try to recognize that interplay and develop employees’ careers in tandem with the company.
  • Offer aspiring managers resources. New and aspiring managers need support and encouragement. Along the path to management, they’ll need guidance, reading materials, coaching, mentoring and a timeline to promotion.

Craft the Leadership Development Program (LDP)

Once aspiring managers have been identified, they will require structured training. At this stage, startups should begin to craft a Leadership Development Program (LDP). Ideally, an LDP will provide a solid foundation of management principles that are both aspirational and practical. If you lack in-house resources, you may consider partnering with a leadership development expert. For example, at Affinity, we worked with Kati Ryan of A Positive Adventure. She helped us create a program that was customized to our business. If you don’t have the budget for an outside consultant, an HR coordinator can facilitate something similar and leverage the executive leadership for support.

A great LDP will align with your values and philosophies of leadership, and integrate relevant content that targets business goals. I’d recommend the below steps to help you create your own LDP:

  • Survey all employees. You’re likely doing a regular engagement survey anyway, so add in a few questions focused on your managers. What do employees think your managers do well? What could be better?
  • Work with leadership on the participant list. This program should include new and aspiring managers. Some companies also include senior leadership, since in many small startups these may be new managers as well. However, if direct reports are in the same program, this may not be conducive to a safe and open training experience.
  • Review your core values. Do they reflect your culture and reinforce good leadership behaviors? These are the rubric by which success ought to be measured within your organization. When building your LDP, take care to consciously integrate these into the curriculum. 
  • Define your management philosophy. Does your leadership team have a clear definition of what it means to be a manager at your company? Once these core tenets have been established, you can also integrate them into onboarding and annual reviews. The LDP ought to reinforce these philosophies so that leaders build the muscle right from the start.
  • Align the training with your business objectives. Is your business focused on new markets this year? Revenue growth? Fine-tuning your core product? All of the above? It might be possible to help the LDP participants structure their goals to align with these broader objectives.

Learn More: What Is Voice-of-the-Employee Technology? Definition, Benefits, and Solutions

Encourage accountability

After the Leadership Development Program has been executed, it’s important to follow up and hold everyone accountable. How do you know these managers are doing a good job? How do you help them maintain their strengths and improve their weak spots? Here are a few ideas.

  • Encourage mutual accountability. It’s helpful in both a formal and informal training scenario to encourage new managers to come together and hold each other accountable. They will be able to share ideas, tackle problems, discuss new learnings, etc. This can be a productive exchange and that helps reinforce their learnings.
  • Set measurable, actionable goals. Most people thrive when they have goals and measurements of achievement. The same goes for milestones around leadership development. New managers should set goals that are related to how they want to improve as a leader, such as:

    • Sharpen meeting facilitation skills  
    • Commit to a regular cadence of 1:1s with direct reports
    • Be a better guide in the feedback process
  • Hold ongoing leadership development workshops. As new managers are promoted and new employees enter the company, it’s critical to revisit the leadership development process. Some startups choose to host full LDPs on an annual or bi-annual basis, with smaller workshops at more frequent intervals. Decide what is best for your team based on participant feedback.

Continued success

Learning and coaching shouldn’t stop after one LDP or one training course. Becoming a better leader is a continual cycle, layering education upon experience and branching into new areas as roles expand. That’s why it’s critical for companies of all sizes to invest in strong leadership culture. By fostering open communication and designing a management track that aligns with your employees’ goals, you will create a cohesive group that is eager to learn. Through the LDP, goal-setting, and regular performance reviews, you will ensure that new and aspiring managers get the tools they need to thrive.
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