Experimenting with different hows for the same why

For nearly eleven years, 95%+ of my writing during weekdays happened in the morning. Writing out a post for a day was a key part of my morning routine.

Since April, however, I’ve been writing in the evenings and it has become a key part of my evening routine.

Similarly, for a few years, I used to take a lot of care to start with thinking about my post for the day vs. getting to my morning news and feeds. Of late, I’ve switched that up to start with morning news and feeds followed by email.

There are reasons for both changes. Part of the motivation was to mix it up and try something new at a time when there was a lot going on. The other part followed a realization that the new routines flow easier with that of the kids’. The end of the day, for example, has become ideal for reflection given their long and calming bedtime routine.

I have no idea if these switches are for the short term or the long term. I’ve learnt to become a lot more flexible about the “how” as long as I’m clear about the why and accountable for the what. For example, as long as I’m clear about why writing here matters and ship a learning every day, I don’t need to micromanage how I do it.

This approach turns out to be pretty useful when we manage ourselves.. and just as useful when we manage others too.

People problems are generally system problems

Consider a few situations that we’ve all likely been through.

a) A few folks on your broader product team seem to frequently spend their time chasing crazy ideas with no result to show for them.

b) You are working on an initiative with folks across multiple teams and find yourself constantly dealing with issues related to miscommunication.

c) You have a cross-functional partner who can’t seem to stop sending you new requests.

d) Your sales team just doesn’t seem to be cooperating.

In each of these situations, it is tempting to think you are dealing with people problems and that the solution is to simply isolate the characters involved and “deal with them.”

In truth, however, each of these could either be partially or completely fixed with better process/systems. a) The product team would spend their time better if the planning process was more rigorous, b) the multi-team initiative needs regular alignment meetings where the issues are consistently surfaced, c) the cross-functional partner needs to be made aware of your priorities (a shared doc?) and could benefit from a light-weight requests process, and d) the sales team likely needs better incentives to cooperate better.

Good management – whether within your team or in your project – is less about dealing with individual people and their preferences and a lot more about thinking in systems that will solve the people problems you face.

And, the first step to being that systems thinker is to be able to say – show me the people problem and I’ll show you the system problem that is the actual root cause.

Managing expenses on Google Spreadsheets

There are many personal finance tools that help automate managing our expenses with fancy graphs and stats on our expenses. Mint, for example, uses data from your credit cards to generate graphs about your spending across categories. Each of your credit card apps likely do so too. But, if you’re in it to be on top of your expenses, I’m still a big fan of managing expenses on a Google Spreadsheet.

I’d shared a simple Google spreadsheet template in a post on calculating expenses 6 years back. We still use an evolved version of that template (happy to clean up + share an updated version if it is valuable to you). And, managing our expenses involves entering each expense. This process has friction built into it by design because the friction inspires consciousness.

We get all the other benefits – we always know exactly how much we’ve spent across major categories. And, we have a wealth of historical data cut in a way that makes sense to us.

We recently compared notes on how we do this with a couple of friends and they tested the “old fashioned” spreadsheet approach as well. Their first reaction after switching was that their spreadsheet made them acutely aware of the areas where they wanted to minimize expenses. This is so true – it is effective to the point where you soon realize you don’t need a budget.

Every technology tool creator’s goal is to make our lives more convenient. But, it is on us to both find the right tools and add the necessary amount of friction to use these tools consciously.

And, as far as topics that are as important as personal finance go, the more the consciousness, the better the long term outcome.

Whoops and Duke management lessons

Tomas Tunguz, a venture capitalist at Redpoint, has an old and interesting post about what a dog and a monkey that taught him about management.

When he was at Google, the 75 person AdSense Operations team used to gather every week for an All Hands. And, along with an update on how they were doing, the meeting always features two stuffed animals – Whoops the monkey and Duke the dog.

When Whoops the monkey was summoned, a handful of team members would retell stories about a mistake they made during the week – once or twice, these were million dollar mistakes. The group would then vote on a winner and that person would have Whoops in their cubicle that week. Then came Duke the dog. Now, team members would share stories about team members who went above and beyond their call of duty.

Whoops helped create a culture that value learning, openness and support and Duke ensured collaborative effort was recognized and celebrated.

I’ve seen variations of “Duke” in meetings over the years. But, I’ve rarely seen the equivalent of “Whoops.” I can see how it would be a powerful way to encourage a growth mindset. I’d love to give it a try.

It probably doesn’t need force

There’s an unsaid rule when you are assembling an appliance or a piece of furniture – the right tools and technique work much better than force.

If you’ve tried applying a lot of force to align edges or to ram screws into pre-drilled holes, you’ve experienced this. When force seems to be the only way through, it is likely you need to go back to the manual or find a different tool.

It turns out that solving people problems isn’t all that different. While there is the rare occasion when force is useful, for the most part, it serves as an indicator that you are doing something wrong. Technique in working with people is making the effort to understand those you are seeking to influence and employing a combination of humor, care, systems and thoughtfulness.

When in doubt, choose tools and technique over force.

Understanding management debt

Ben Horowitz, the former CEO of Opsware and now-successful venture capitalist, has a great post on management debt. He offers a slightly deeper explanation in his excellent book – The Hard Thing About Hard Things.

I have been thinking about management debt over the past few months but didn’t have a term for it. I am now able to put the word into context and would like to share some of my lessons.

Management debt is when a leader or manager (I will stick to “leader” for simplicity) takes a call that works better for the short term than for the long term. Any such decision is equivalent to the leader taking a loan for a short term pleasure and will require the leader to pay it back with interest. The rates of interest on certain kinds of management debt are really high. In his blog post, Ben details 3 situations where he’s seen management debt –

1. Putting two in a box – Trying to keep two talented folks in his company during a reorganization by making them co-heads.
2. Over compensating a key employee when she has a better job offer because she is key to a current project.
3. No performance management or feedback process – leading to surprises when things don’t work well.

I haven’t managed a billion dollar company and, while I am sure my experiences don’t compare to those of Ben Horowitz, I have found myself guilty of using management debt multiple times without realizing it on multiple projects. And my lessons are as follows.

I. Define culture early – it is hard to change. Culture is set by a set of principles that defines your approach to work. This needs to be defined really early or things get really messed up down the line. One such example is a project I’ve lead for nearly 3 years – when we started, we took a scrappy approach towards getting things done. I figured that the focus ought to be to just get results and we’d find time later to define how we’d like to do it better. So, we took nearly a year to define our values, ways of working, etc., and just kept the habit going. And, you know what? 1.5 years later, we still haven’t gotten past our scrappiness. Heck, we don’t even know what our values are.

The extent of the damage is evident because another member this team and I are also part of 3 other project teams and we behave differently in those. Culture is powerful and is hard to change once it is set. I am still not clear how to solve the problem with the culture issues in this project – clearly, I’m still paying the interest on my management debt.

2. Create a 6 month feedback process. I’ve worked on projects where there was an attempt at weekly performance management and then run projects with no performance management. I find that a 6 month feedback process is reasonable and important. 1-3 month feedback can work okay on short engagements but feedback systems shorter than that become carrot-and-stick systems in my view and don’t give people enough time to get comfortable. If you think this is hard to do in a busy day job, I can assure this is harder when you are working on a project(s) in addition to your day job on weekends with limited time. That said, it is important. Else, you are just taking on more debt. And, I have learnt that the interest on this one is costly.

3. Create a list of management principles. As I’ve been thinking about 1 and 2, I’ve realized that what I am missing is a list of management principles. I have an implicit list but it’s clearly not been enough to provide clarity. These management principles will help you stay true to your goals and will ensure you are firm and insistent on the right things. Once you have these principles defined, don’t compromise.

I am going to explore this topic in greater depth over the next few months. More to follow on setting culture, designing feedback processes, developing management principles, and the like.