Working effectively as I try to be successful

In this series, I will focus on real-life perspectives; relate topics to what I am doing, people I have met, thoughts I have had. I, like anyone, don’t know what will happen, but I do know better than anyone else in the world (!) how I approach the problems that I face. Hence, that’s where I will focus. I will certainly share some of my predictions as well, but will always try to do it in the context I am in.

This is my fifth year as CFO at Planhat. When I joined, I had spent the first six years of my career learning about business and software on the investment side. I really enjoyed it. I was fortunate to work with a few leaders that I respected and learned from. Some I am still close with. The nature of focused and intense projects, having the opportunity to observe and listen, often being the person least knowledgeable about the topic at hand (with resources to leverage more experienced people), iterating quickly, suited me really well and I learned a lot. What I learned, and how I learned it, shaped how I approach problems and how I work today.

I later joined Planhat. How I joined Planhat is for another story, but when I joined Planhat, I had no real operational experience. I had observed successful companies, worked relatively closely with leaders of companies with much more experience than I had (or still have), but I had not been part of building a company at any scale before. That said, I had learned a thing or two working as an investor, and as it was early days for Planhat, I never felt that was a problem.

I also had a healthy degree of naivety combined with excitement towards the product, team and opportunity. I was excited about the world moving towards recurring business models and software growing as a sector. I had spent a lot of time on projects to increase retention; if we could increase retention, growth and valuation multiples would increase, and we would make more money.

I was incredibly excited to join a team of entrepreneurs more experienced than myself. I have learned so much from Niklas Skog, Kaveh Rostampor, Chris Regester, and many others at Planhat over the past years.

P1: Erik, Chris. Malibu. 4 am PT, every trip with Chris; P2: Kaveh, Yaro, Niklas. Santa Monica. January 2022.

As an early article in this series, it seems appropriate to give my perspectives and reflections on customer success. Helping drive successful customer outcomes is what we do at Planhat. I will dive into that in my next article.

Today, I will give my perspectives on something I have been thinking a lot about recently: What works for me as I try to work effectively, and ultimately how I try to be successful. In this article I have outlined some perspectives on what works for me.

Mountains of Pacific Palisades.

(1) Find belonging, ownership and purpose

Let me start with something that is not a way to approach a problem, nor a way to work effectively, but rather a requirement in order to achieve my goals. For me, probably the most important requirement: A sense of belonging, ownership and purpose.

Doing a good job over a long period of time, without a sense of belonging, ownership and purpose, is very difficult. In the jobs or projects where I have done well, this has always been true.

As an investor, I remember getting feedback from my boss that I did a bad job in a project where I didn’t believe in the deal we were pursuing. He said, ”Erik, you are fantastic when you believe in the purpose, but you come across as bored and passive when you don’t”. I took the feedback to heart and thought, “I need to do better when I don’t believe in the purpose”. I tried a bit harder next time, but a few months later he said the same thing. I am not sure if I understood back then, but in hindsight it’s very clear. The solution was (obviously) not to do more and better without purpose. The solution was to find purpose. Luckily, this was the case in many of the projects that I was part of.

At Planhat, I have always felt a sense of belonging, ownership and purpose. During different parts of our journey, it’s been demonstrated in different shapes and forms, but it has always been true and very important to me.

Without this feeling, it is very difficult to be inspired to work hard. It is also not fun. Working is a big part of all our lives, especially for those of us that want to be successful. Without a purpose, work will almost certainly become a negative experience. Personally, I want a job where I get inspiring ideas when lying awake in bed late at night or when I’m in the shower.

The Planhat team. August 2023.

(2) Listen (well!)

We have all been told about the importance of listening. If you ask around, most people consider themselves good listeners, similar to how a majority think they're above-average drivers. From what I've observed, this isn’t the case - people tend to be worse listeners than they think. Too often, people are planning their next comment rather than actively listening and thoughtfully reacting to what has just been said. To some extent, this is perfectly natural, as making one’s voice heard in some cases has value in itself (at least perceived value). The irony is that in the effort to be heard, the essence of what makes communication valuable is often lost. When everyone is more concerned with speaking rather than listening, the opportunity for genuine understanding and collaboration diminishes. It becomes a competition for airtime rather than an exchange of ideas.

This is not new, you know this. Everyone knows this, but very few of us are able to translate that knowledge into action, let alone an improved behavior. I am not sure if I am a good listener or not, but I really do make an effort, and when I do, I learn.

As an investor, you are fortunate to have a lot of natural opportunities to observe and listen. The job is literally to listen and evaluate. To give a very concrete example; imagine you are 26 years old. You are (part of a team) assessing an investment into a $200 million banking software company. Your day looks like this:

Being the least knowledgeable person about a topic means opportunities to listen and learn.

Throughout the day, you are the least knowledgeable person about essentially every topic. That’s a great position to be in. Obviously, not every day looks like this, but I am trying to make a point. For me, this meant an incredible opportunity to listen and learn. Being able to leverage resources much more experienced than me meant being on steroids, allowing me to maintain a steep learning curve (which, in my opinion, is one of the few things to really care about in the early years of your career).

Now, listening when you have answers everywhere is in many ways different from listening when you are early in a company, on your own, the only one knowing what to do. That said, when you as part of leadership are building a company, listening is still about about capturing unfiltered insights from smart people around you. It's about gathering raw, honest perspectives, filtering those perspectives, getting ideas, and ultimately using those perspectives and ideas to develop refined ideas that can guide your decisions. Actually not that different.

Jeff Bezos was on the Lex Fridman podcast in December. It was a great episode. He spoke very intelligently about the importance of listening, but also about his role in meetings.

“There are little things you can do. So for example, in every meeting that I attend, I always speak last. And I know from experience that if I speak first, even very strong-willed, highly intelligent, high-judgment participants in that meeting will wonder, “Well, if Jeff thinks that, I came in this meeting thinking one thing, but maybe I’m not right.” And so you can do little things like if you’re the most senior person in the room, go last, let everybody else go first. In fact, ideally, let’s try to have the most junior person go first and the second and try to go in order of seniority so that you can hear everyone’s opinion in an unfiltered way. Because we really do, we actually literally change our opinions. If somebody who you really respect says something, it makes you change your mind a little.”

(3) Be in the weeds

Next, I have learned that in order to successfully work with my teams, I need to (try to) be deep into topics and really understand things in detail. This may sound obvious, but from what I have seen, this is not always true for leaders. Personally, I struggle when I don’t understand the details.

In my opinion, this is incredibly important for all leaders - to be in the details, to lead by example and to show intensity. I mean, really getting into the weeds. To understand how things work as well as anyone else on your team. For me personally, this means trying to understand or trying to being good at:

1. Filtering limitations in our CRM

2. Configuring the more complicated tracking in Google Tag Manager

3. Detailed SaaS KPIs definitions; understanding why certain definitions make sense for different businesses, our business, and our customers

4. Troubleshooting underperforming keywords in Google Ads

5. Details of our 2024 IFRS implementation project

6. Designing beautiful slides and writing detailed, well-articulated, internal memos

7. The list goes on...

A few weeks ago, I was in a meeting with a group of scale-up CFOs, all managing companies with between 100 and 500 employees. The discussion was about being too reliant on key people, having leaders too involved in deals and not being set up to scale. Of course, I understand this ambition. Companies need to prepare for being bigger.

At the same time, sometimes I think leaders need to forget about scalability. They should instead be far down in the weeds. Honestly, many of the most successful managers I see (at Planhat as well as among customers) are micro-managers. Micro-managers up to a certain point and with a certain style. Micro-management should of course be done in a supportive and inspiring way - leading by example. A successful leader will be able to move up and down, set direction with short intense stints in the details, but then move up to a higher level and let the teams work hard to meet their targets. Then down again to calibrate.

(4) Create urgency, ensure accountability, and take risks

About staying effective. In my experience, the following things are critical for me, but probably for any high performing team: creating urgency, ensuring accountability, and taking risks.

First, urgency and accountability. Setting targets helps. A lot. Targets encourage progress. Being relaxed has a bunch of benefits in life, but it is not a good strategy if you want to get a lot done.

Also, targets impact how to approach problems. The time of any project can be cut in half by changing the scope and approach. This realization is very important. For some projects and tasks, you can cut the time by a lot more. In fact, to finish in 20% of the time and still achieve most of the result is possible in most situations. By accepting to sacrifice certain results, or by accepting being wrong a bit more, you can be a lot faster. For many (perhaps even most) topics, this is a perfectly acceptable tradeoff.

Without practical examples, the prior paragraph isn't very helpful. The most obvious, very common example in my and probably your normal workday, where time can be cut by a lot, is in the normal day-to-day meetings. Too often, meetings conclude with: "I will think about this and follow up". This kills momentum. This often means the next follow up on the topic is next week. Instead, do everything you can to solve the problem now. On the call. Share your screen and take notes together. Or even better, sit in the same room. Extend the meeting if you need to. By doing this, the topic may be resolved in 1 hour instead of 1 week.

Cutting time is very effectively done by setting ambitious (sometimes unrealistic) targets. At the same time, high expectations need to be balanced with the risk of creating fear. Fear can kill creativity and progress. Fear means people will not take chances, not challenge their colleagues and not think outside the box. It is all about that balance, and if you are a leader that ensures belonging, a leader that listens, and a leader that leads by example, you can set extremely high targets.

At the end of the day, the reality is that most people get the most done right before a deadline.

Taking risks. Getting (good) stuff done is difficult and requires taking risks. It requires risking failures along the way. And failures will certainly happen.

Risk is not necessarily about making a financial bet with the opportunity to gain or risk to lose money. In this context, risk is about taking chances on what to spend time on. It is about going into uncharted territory where the path and end result is not entirely clear.

This is something that at least I underestimated in the past. Getting good stuff done requires trying, failing, and trying again. Early on, certain initiatives may make sense or even seem like a great idea. For some initiatives I run with, I realize half way in why it was a bad idea. It can be for reasons impossible to predict and may not mean focus was wrong; sometimes reality changed, or priorities changed. At the same time, sometimes I run with something and it ends up adding A LOT more value than expected.

Keeping velocity and testing ideas, asking for early feedback on work you have done, rather than waiting for the perfect moment (or for someone else to do your job) is certainly the way to go. This article is a good example. The end product was initially not clear, but after testing some early concepts, a few iterations of drafts, and good feedback from a select group of people, the end product evolved into something that made sense for me.

Honestly, I really didn't understand this before Planhat.

P1: Presenting some of my thoughts on the SaaS markets. Spring 2022; P2: Erik, Kaveh. NYC. Spring 2023.

(5) Work hard

Finally, in order to be successful, you need to work hard. You need to work a lot of hours. This has been said a million times, but in my experience there is no way around it.

In fact, I think that people claiming that you can be successful without working hard are kidding themselves, especially early in their career. Sam Altman wrote a great article on the topic; How To Be Successful.

“I think people who pretend you can be super successful professionally without working most of the time (for some period of your life) are doing a disservice. In fact, work stamina seems to be one of the biggest predictors of long-term success. One more thought about working hard: do it at the beginning of your career. Hard work compounds like interest, and the earlier you do it, the more time you have for the benefits to pay off. It’s also easier to work hard when you have fewer other responsibilities, which is frequently but not always the case when you’re young.”

Working hard is not easy. It inevitably means making sacrifices. It also needs to be sustainable for it to work over long periods of time. Working sustainably will mean different things for different people. Ultimately, it requires a sense of belonging, ownership and purpose. It requires a match between the person and the job. Without this, it is very difficult to be inspired to work hard. It is simply not fun.

Thanks for reading this article. These are some of my perspectives and learnings on a topic I have been thinking about recently. I will over time share more perspectives around challenges I face, conversations I have, and ultimately how I try to improve and learn.