To Manage, or be Managed

As someone who has had the opportunity to manage teams of 100 or more individuals, as well as being managed, I have gained some experience and knowledge that I hope can be useful to others. Through trial and error, and a willingness to learn from my mistakes, I have developed a few mental models that have helped me to navigate the challenges of leadership. In this post, I would like to share ten insights with you in the hopes that they may prove helpful in your own professional journey.

Feedback: It has been my experience that a manager doesn’t need to be a subject matter expert in order to effectively support their team members. Rather, I believe that a manager can be thought of as someone with a generally sound understanding of the relevant domains, who has the opportunity to regularly observe their team members in various professional settings. Through proactive attention to their team’s behavior and performance, a good manager can offer timely feedback that can help their team members grow and develop. While some feedback may be more accurate than others, and there may be times of disagreement and pushback, the true value of a good manager lies in their consistent flow of suggestions and encouragement for improvement. Feedback is a gift, and the more receptive we are, the more we’ll receive.

Promotion: Think of the importance of the term “promotion” in a different light. Rather than viewing Promotion (with capital P) as the discrete event where an individual’s title and compensation increase, I believe that a great manager is always thinking of ways to promote the work of their team members. Like a talent agent, a good manager is interested in finding new opportunities for their team to showcase their skills and contribute to broadly important initiatives. This is not about indulging individual pursuits such as attending a conference or work trip, but rather about finding the intersection between an employee’s strengths and the company’s needs. This can be achieved by associating a person with an already important project, or by highlighting someone’s less apparent work to the rest of the organization. When done effectively and consistently, this practice will lead to actual Promotions organically.

Scope: The other side of the coin is that individuals should be looking for scope and impact, instead of title and money. Companies and their leaders tend to operate rationally over the long term. If an employee becomes pivotal to the success of the organization, the leaders will conclude this person must be retained, and will structure their compensation accordingly. If an employee improves the impact of a team whenever they are involved, then it’s only rational to give them more opportunities for leadership. An ambitious individual should ask for opportunities to have more impact and be patient with the rewards. Asking for a raise or a promotion rarely works as intended. The corollary to this is that managers should be shrewd and proactive about identifying these rising stars, and have the courage to elevate them quickly, even as more tenured employees who are “ahead in line” grumble.

Compensation: Open and honest communication between employees and managers is important when it comes to discussing promotions or raises. However, it’s best not to bring up this topic casually and unexpectedly during a one-on-one meeting. Instead, employees should let their manager know in advance that they want to discuss compensation and come prepared with data to support their performance. Managers should also take the time to prepare actionable feedback for the employee. It’s unlikely the first conversation will lead to an immediate change in compensation, so one should be prepared (and satisfied) to walk away with concrete areas for improvement. Companies usually have performance management processes in place, so it’s best to work within that framework and focus on delivering results in the meantime. It’s also important to keep in mind that compensation for a role is determined by the free market.

Tactics: To maintain productivity, it is crucial for managers to balance their strategic responsibilities with a tactical mindset. Even as they progress to more abstract roles, managers should stay connected to their team’s functions and become familiar with new roles to ensure they have a solid understanding of their team’s operations. Managers can stay in touch with the details of the organization by asking pointed questions and regularly reading relevant documents or other artifacts. For individual contributors, it’s important to recognize that while managers are not in the trenches, they probably have strong pattern matching and can intuitively highlight potential issues. As they say at Amazon, leaders are “right a lot”, so ICs should be prepared to dive deeper when confronted with skepticism.

Communication: As teams grow larger, managers need to be aware of a greater number of factors. It’s important for employees to recognize the asymmetry in scope between themselves and their managers and not assume that their manager (or manager’s manager) knows everything about their work. Don’t assume they are aware of critical risks, upcoming deadlines, or important accomplishments. Employees should communicate critical information explicitly and repeatedly. Better informed leaders make better decisions and that benefits employees and customers. Managers, on the other hand, should not assume that all employees understand the importance of various strategic initiatives. Regular and well-articulated updates are necessary to ensure that team members are making the best use of their energy and resources.

Partnership: It’s best to think of the relationship between an employee and their manager as a partnership. Managers who think too hierarchically and employees that only do what they are told, will not get the most out of their relationship. Unless a manager is intentionally exerting their authority, it’s best to think of them as a team member with various responsibilities that complement your own, so you should both be coordinating how to tackle important issues together. By the same token, while managers should invest in the development of their team members, employees should also help their manager succeed. When your manager wins, everyone wins. If a manager gets promoted, that gives them more latitude and resources to help the team achieve goals, and also creates a leadership vacuum for others to grow into.

Longtermism: Professional journeys are very, very long. If you are lucky, you will develop a strong network of close connections, which will grow stronger with time, and become more powerful as each participant pushes forward in their career. This is probably the main reason to choose a great startup over a large company, in spite of the risk adjusted ROI. Your success could depend on hiring someone you’ve worked with or going to work for someone who used to report to you. Someone in your network might be the first investor in your next company, or provide a piece of critical insight that gets you unstuck. Alongside knowledge (and unlike damage to your DNA), the value of your network can have positive compounding effects for the rest of your life. So don’t burn bridges and stay in touch with the people that you respect (and definitely don’t write a LinkedIn post berating a past manager).

Until the next one.

image credit, Midjourney: “shakespeare play with hamlet, wearing a business suit, talking to his skull, social realism style” (and then some iteration to get the right concept)

~~~ I asked my LLM of choice to complete the post to make sure I wasn’t missing anything critical. A few more basic, but important tips below.

Delegation: A great manager knows how to delegate tasks effectively. Delegation means trusting your team members to take on responsibilities and complete tasks with minimal supervision. Delegation allows managers to focus on higher-level tasks and ensures that team members are empowered to grow and develop their skills.

Conflict: Conflicts can arise in any workplace, and a great manager knows how to handle them effectively. Managers should create a safe space for team members to voice their concerns and work towards a resolution. By addressing conflicts promptly and fairly, managers can prevent them from escalating and impacting team morale and productivity.

Accountability: A good manager must hold themselves and their team members accountable for their actions and results. They should set clear expectations, provide regular feedback, and follow up on commitments. When things go wrong, they should take responsibility and work with their team members to identify the root cause and find solutions.