Office Hours #3 — Managing More Senior Hires

Ideas on how to manage people who have more experience than you

This is the third installment of the weekly Office Hours series, where I explore common questions raised in discussions with engineers within and outside of Xendit.

One of the hardest challenges that we had to overcome in our early days was hiring and managing the right senior managers for the organization. All of the founders were first time founders AND first time managers which means we didn’t exactly know what good even looked like.

This is an incredibly dense topic that can’t possibly be boiled down into a single post. I will focus on the high level ideas which I believe ultimately allowed us to successfully build a senior management team within engineering and save the tactics of sourcing, hiring, compensation, etc for a future time. This post is primarily aimed at managers who are in the process of scaling themselves and their teams and are putting in managers who on paper have more experience and are more “senior” than they are.

The mindset that we use to approach this is:

1. Seniority is a function of customer understanding and ability to drive customer value
2. Senior managers need to build trust upfront and be in the details
3. Senior managers need to be held accountable
4. Senior managers need to be coachable
5. Senior managers need to be natural ambassadors of culture

Let’s break each of these down.

Customer Understanding and Value

As someone who is planning to bring on a senior manager directly under them, it’s likely that you’ve had some tenure already at the company. It’s assumed that you’ve already seen some share of customer pains and have solved them. It’s assumed that you would be able to address customers by name and that your work has contributed in a visible way to the growth of the business.

If these preconditions are not met, it’s unadvisable for you to consider bringing on a senior manager under you. At Xendit, we believe that seniority (in management) is a function of how well you understand customers and how well you’re able to solve for them to ultimately drive business value. Regardless of how many years of experience or domain knowledge someone holds, they will always be outranked by someone that actually has demonstrated a strong track record of delivering for the customer.

Meeting these preconditions means that you’ll have the confidence to direct your new manager towards the right problems and to put it bluntly, “call bullshit” when they cannot justify how the work and plans they’re proposing will be used to address the customer problems that the business cares about. Any great senior manager hire should be better than you in many ways and should have more skills, experience, etc than you. That just means you did a great job in hiring. However, it’s highly unlikely that they’ll know as much about the business, product, and which customers are important because that context takes much longer to build and that’s what you should already be strong at.

Build Trust Upfront

We believe that the first 3 months of a senior manager’s tenure is extremely important and ultimately determines whether this person will stick around for the long term. Within these first 3 months, we ask senior managers to demonstrate tangible value by getting their hands deep into important problems across the org. This may seem counterintuitive because many people assume that senior managers should take a broad view and not concern themselves with all of the details. People assume that senior managers that dig into details are perceived as micromanagers.

Our reasoning for requiring this goes as follows:

1. If the senior manager really cannot understand the details, they will not be able to make the right strategic decisions
2. Respect is earned when managers demonstrate that they can ADD VALUE to the day to day experience of their team members. No one wants a new overlord, especially when this new one would replace their existing manager where trust has already been built to some extent.
3. The senior manager’s performance can be easily measured. When someone proposes a plan that is too long term, you can run into cases where lack of results can be explained with the phrase “that’s expected because my plan is a 4 quarter plan so results aren’t expected until later”. Then those goalposts can continue to move until you realize that you’ve wasted a good year and have thoroughly demoralized your team.

Accountability

If you’ve hired a competent senior manager, your job should primarily be holding this person accountable. The transition from being directly accountable for results to holding someone else accountable can be turbulent at the start. There can be a bias towards having the new manager strictly follow all existing practices and procedures but this is counterproductive when taken to the extreme. You’ve hired a senior manager to take ownership of outcomes and they need some creative freedom and to draw from their experiences to effectively deliver.

Our recommended approach with managing senior managers is to:

1. Set clear measurable targets (SMART goals can be a good place to start)
2. Get buy in, iterate, and ultimately agree on a set of targets and timelines
3. Track on a regular basis and do reporting (we do this monthly with our senior managers)
4. Hold them accountable to hitting milestones and the final target
5. If any adjustments need to be made, they need to be made in advance and APPROVED by you

Coachability

We believe that senior managers must be coachable. This is especially true in a high growth startup environment where the scope of the problem grows by an order of magnitude every few months. This is also true when local cultural understanding and sensitivity is important. A senior manager that charges in guns blazing and completely set in their approach is unlikely to make much headway for very long.

To test this, during our interview process, we spend an inordinate amount of time and effort on writing detailed feedback and reviewing that feedback with the candidate to see how they take that feedback. Successful candidates will seek first to understand that feedback before reacting, then will work with you to align on which feedback they will accept and action. Then you should be able to track that action item through the rest of the interview process and see if they’ve made the tangible changes they’ve committed to. This is a really time intensive process but is very important for when you’re hiring a senior manager.

Cultural Ambassador

Culture is really important to every company, whether it’s explicitly understood or not. If you’re in the market for a senior manager, it’s even more important to ensure that they’re a living, breathing embodiment of your culture. It takes too much time to change someone at a cultural level and while that time investment may be worth it at a junior level, attempting to do so at a senior level will result in many wasted cycles and disappointment from the team.

Xendit has a trial process for each new hire, and this is even more crucial for senior manager hires. Forcing continuous interaction over 2–3 days means that it’s harder to hide many of the automatic responses and habits that people have built up over years. It allows for the potential for mistakes and miscommunications to happen and to see how candidates address and resolve them. It allows for more open and honest communications when someone is not in a performative mode because that is the normal state most people are in when working.

Conclusion

Hiring senior managers is hard, especially when you don’t have any experience doing so. The ideas presented above have evolved over years and hopefully can reduce the pain you experience when going through this journey. However, these ideas alone won’t guarantee success. Setting clear expectations and measuring often will ensure that after you’ve given someone a fair shot, you will be able to “fail fast” and remove an underperforming senior manager. Not doing so can be highly damaging to performance and morale within your teams.