Love Letter #8

Bootstrapping: Why Business Discipline is so much harder than Personal Discipline

My wife tells me that I’m the most disciplined person she knows - this might be true (in terms of the people she knows), but I know I’m far from getting a gold medal in the field. With that being said I believe personal discipline is a muscle you work on daily. It is that daily war on your shoulders between your inner angel and your inner devil. Hopefully, one day you wake up and your inner angel is so buffed up, that your inner demon does not stand a chance. It is the fight of a well-fed lion against a starved one.

Like a muscle, to some people and in certain domains, discipline comes easier than to others. The example of food or exercise comes to mind.

However personal discipline has a special characteristic: it is binomial. Something is either good for you or bad for you. And the clarity of these choices is starkly clear: veggies are good, hot dogs are bad. You can choose the hot dog, but you are kidding no one: you know it is bad. You didn’t read, you know it is bad, you stayed in bed, you know it is bad. You didn’t exercise, you know it is bad. And so on…

But business discipline. Shit, man. These choices are not clear at all. And the more responsibility you have, the fuzzy the choices become. You have to choose between keeping up your forecasted budget or reacting to an idea that can bring you more money. You have to choose between tackling technical debt, fixing bugs, or building new features. You have to choose between more hiring or imposing a higher workload on people, or firing people who are underperforming. You have to choose between keeping intact those KPIs that investors, “the experts”, and LinkedIn say are “best-in-class”, and doing what you feel the business needs. The hard thing about business discipline is that the choices are all good, you have to do them all. If you don’t do them, someone will suffer: it is either your business, you as a CEO, a team, or a specific employee. To add to this, some of these are false choices - meaning that there is always a third choice, that is also good. So you tell yourself: I’m just not being creative. This is why CEO is the loneliest role - your problem is always different, because your company is different, and because only you have the full view. I know, I know… Cry me a river…

I’ve decided to write this so I can explain to myself this concept, walk it through from the point of view of several roles in my organization, and see if I can make sense of it. What does business discipline mean for each person in these roles. Hopefully, this will shed some light on both my path and yours.

Let’s start with the positions whose workload is pushed by the movement of the organization: Customer Success and Project Management (implementations)

Customer Success:

Standard situation:

Lots of emails, lots of questions to answer, it consumes you. On top of this, you have your upsells to make. You have to grow your accounts. Oh, and if they churn: your fault. Not really, but yes. By all accounts it is the literal definition of the “rat race”, the fucking rat running wheel.

But here, hopefully, you are heavily paid on commissions. Hopefully, your boss is telling you: hey, it is your business, grow it. Is it hard? Hell, yes, is hard. But life is hard. Tough luck!

What are the hard choices here: if I don’t answer this email, the client is going to think I’m not responsive or I don’t care. If I don’t spend time on this issue, the client is going to churn. Well-documented cases? Fuck it! I already logged the email in the case, let me put out the other fire. The end of the month arrives, and you’ve won some battles and lost some others. The client renewed, puf, my portfolio is saved. Did you win? Who the fuck knows! You were too busy to keep up with the score! Next day? Let’s get on that rat wheel again.

So here is what discipline could look like (from the naive point of view of your CEO). Because you are paid on commissions, you want to grow your portfolio. That means working high-maintenance accounts so they can become low-maintenance accounts. The good news is that these accounts don’t want to be high maintenance; the total opposite, they want to be low maintenance. They don’t really want to talk to you. The best service is the service you don’t need!

So here’s what you do:

First, make a list of the things that move the needle for you and your client:

  • Understand how your customers work

  • Understand how your company works

  • Explore accounts growth opportunities

  • Decide the five things that you want for your client during the next six months (five, and no more than five, your hand only has five fingers)

  • Document correctly all your cases so you can keep the product management on their toes

  • Give to your Customer Success lead all the responsibility for the dumb shit you have to do every day. It is their job to make your job easier, and not harder. Their job description is to literally help you scale. If they are not doing this, get them fired. We are a team, not a family. We want to win. Remember, you are tired of the rat wheel

  • Make a list of the top 5 issues that are taking most of your time, provide two or three solutions on how to solve them, and take it to your leadership team (CEO, CPO, Finance team included). Make them feel ashamed. Shame is a powerful motivator! Send it to them every month until they fix it. Also, be specific: don’t say - I have too many calls. That’s both lazy and unhelpful. Believe me, if your leadership is good, they will hear you. You are creating what is called “positive tension”, or “positive pressure”. They don’t listen, you repeat, and keep repeating.

You make a list of the things you don’t want to do. Think of the things that you think are unfair to you.

  • A product issue has come up, or a lack of feature has come up from the client. Dear Product Manager, why do I have to answer this question? Can you please jump on the call with me and explain to the client why we don’t have this? Make her/him feel the pain

  • Why am I spending time debugging this client? Dear Customer Success Director, can you explain to me why am I doing this and not the support department?

  • An email that could have easily been solved with a product article is not there - dear Product Manager, here is your escalated case for lack of documentation. Thank you, let me know when is ready! Put a lot of smile faces, here.

  • Bad implementations? how many times do we have to go through this? Dear Implementation Manager, Why? Why? Why?

This is hard. I know it is hard, it is fucking business discipline! You don’t want to be mean. You don’t want to be an ass, or difficult. But you have a job to do. You have a life to live. You don’t want to be late at night or on the weekends answering client’s emails. Fuck that! You want more money and less work. You have to choose what job you want to do: you either want to be answering to clients all the time or on behalf of the client, hold someone else accountable. Only one of those jobs is scalable. This is super hard. But you know what lack of discipline will get you:

Pick. That or a prosperous, fulfilling life.

From the Implementation/Project Management point of view

Standard situation:

Lots of emails, lots of questions to answer, data loading, and configuration requests. Features that were promised and are not there. Oh, and you have to do this on time, along with 5 other implementations. 3 calls per day, when am I going to do this? Oh, the client does not want a single go-live, but 5 go-lives: one for each process. Wait what? So now I have to work 5 more weeks on this project? By all accounts another literal definition of the “rat race”, the fucking rat running wheel.

But here, hopefully, you are heavily paid on commissions. Hopefully, your boss is telling you: hey, the more projects you can deliver, the more commissions you’ll get. it is your business, grow it. Is it hard? Hell, yes, is hard. But life is hard. Tough luck!

What are the hard choices here: if I don’t answer this email, the client is going to think I’m not responsive or I don’t care. If I don’t do this the way the client wants it, she/he is going to be mad, even though we’ve been through this 100 times, and each time everything goes to hell. Well-documented cases? Fuck it! I already logged the email in the case, let me put out the other fire. The end of the month arrives, and you won some battles and lost some others. The client went live, it was painful, but they are live. Did you win? Who the fuck knows! You were too busy to keep up with the score! Next day? Let’s get on that rat wheel again.

So here is what discipline could look like (again, from the naive point of view of your CEO). Because you are paid on commissions, you want to do more projects, you want them to go smoothly. You want to focus on delivering successful projects and have clients singing you praises for guiding them through a process that was supposed to be hell. Here, as a guide, you are in the business of preventing fires, not being a fucking firefighter. Nobody wants a guide that leads you into fires: that is the whole point of getting a guide! In order to do this, you have to have clear communications, lots of resources that are easy for the client to consume. You have to have a team and technology that will help you get these projects off the ground without working nights or weekends. Projects need to be structured and paid fairly. You are the client guide, they need to see the map, the progress. You don’t want them to be like a child driving you crazy: “are we there yet? I’m hungry, I don’t know how to do this, this is too difficult. Where is my report? Why can’t I see this?”

So here’s what you do:

First, make a list of the things that move the needle for you and your client:

  • Understand how your customers work

  • Understand how your company works, your process, a clear step by step process. If there is a question, it is not clear enough. You are going to share this with your client - if there is a doubt, they will ask it. YOU ARE TIRED OF QUESTIONS!

  • Make a checkmark of all possible fires, and follow it as if your life depends on it - why? So you don’t walk into them! So you can have a normal life! So you don’t have to work on the weekends!

  • Document correctly all your cases so you can keep the product management on their toes

  • See your process, and constantly ask, why can’t we automate this?

  • Give to your Lead all the responsibility for the dumb shit you have to do every day. It is their job to make your job easier, and not harder. Their job description is to literally help you scale. If they are not doing this, get them fired. We are a team, not a family. We want to win. Remember, you are tired of the rat wheel, fuck working after 6 pm!

  • Make a list of the top 5 issues that are taking most of your time, provide two solutions on how to solve them, and take it to your leadership team (CEO, CPO -Chief Product Officer-, Financial lead included). Make them feel ashamed. Shame is a powerful motivator! Send it to them every month until they fix it. Also be specific: don’t say - I have too many calls. That’s both lazy and unhelpful. Believe me, if your leadership is good, they will hear you. You are creating what is called “positive tension”, or “positive pressure”.

You make a list of the things you don’t want to do. Think of the things that you think are unfair to you.

  • A product issue has come up, or a lack of feature has come up from the client. Dear Product Manager, why do I have to answer this question? Can you please jump on the call with me and explain to the client why we don’t have this? Make her/him feel the pain

  • Is there a process improvement that will save you one hour of work per project? Why am I doing this? Dear Manager, CEO, CPO, can you explain to me why haven’t we automated this? Why don’t we have this resource ready? Why am I answering this answer over and over again?

  • An email that could have easily been solved with a product article is not there - dear Product Manager, here is your escalated case for lack of documentation. Thank you, let me know when is ready! Put a lot of smiley faces here.

  • Oh, the client needs 20 reports? Why aren’t they there already? Dear technical team, is it smart for me to do this 48 times during the year?

  • How am I supposed to manage 7 projects? Dear manager, dear CEO, Financial team, why is this happening? How come you didn’t bring this up earlier?

This is hard. I know it is hard, it is fucking business discipline! You don’t want to be mean. You don’t want to be an ass, or difficult. But you have a job to do. You have a life to live. You don’t want to be late at night or on the weekends answering clients’ emails, doing configurations or data loads. Fuck that! You want more money and less work. But you know what lack of discipline will get you:

Pick. This or a prosperous life

From the Product Management and Technical Product Manager point of view

Product Management is one of the harder jobs in a technology company. Especially if they have a lot of technical debt. We are great followers of the great Cagan and Lenny, but even with all his books, and podcasts, this is still difficult.

You have bugs, technical debt, new features, and product requests to address with limited resources (people and time). In addition to this, you have your calls with clients, sales calls, and team meetings. Oh, and marketing, of course, man, marketing! If your product is not selling, then what are we doing? Even Cagan said, “if you think this is a 40-hour job, this is not a job for you”.

I was also told that objectives change constantly, and the post keeps moving. But come on, man, you know the main objective. We are here to do one thing: to make money through delivering value. So all Product Managers can think this through: Good money is made through quality products that meet customers' needs.

Quality product, what does that mean? It means a stable product, a low-bug product.

I was told by one of our architects that priorities are always changing - sometimes we are delivering new features, sometimes we are focused on bugs, and sometimes we are working on technical debt. This is not an unfair complaint!

At the end, your product is your game. You need to understand the why of things, the finance of things, the marketing of things. Sure, we can debate strategy, but we all need to agree on it. It needs to make sense. You are the captain of your team, oh captain, my captain. You get something imposed onto you, feel free to fight it. In the long run it needs to meet two conditions: save you frustrations and to take time out of your day. If those conditions do not apply: fight it.

From the Sales Perspective:

Here business discipline involves a very hard and annoying task: listening to your reps' calls. But this is it. This is the entire job. We have to listen to all calls-that is how we know we are taking advantage of every single lead. Failure to do this is a failure to do the job. Sales Management is about selling through others. This is the only way you can do it. If you are not listening to two calls per day, you are not doing your job. Is it hard? Yes. Is it boring? Yes. But the rewards are sweet, sweeter than everything. And once they are done, it is done.

Another thing that is hard, very hard, is to ensure that we are spending time prospecting, building pipeline. 2 new opportunities per rep every week. It is not impossible, but it is hard, really fucking hard. People are rude, they hang up, they are annoyed. But that is the job, that is what will guarantee that we meet our goals, that we keep feeding the beast.

Low quality leads? Not enough leads? Put the pressure on Marketing. What are we doing about it? But remember Kipling: you can count on marketing, but not too much - your pipeline is your own.

Marketing

You are where everything starts, you are the face and voice of the customer, both externally and internally. Make sure you find your voice, make sure it is sure and right. You can find it by listening to the beat of the heart of the entire company. Our story has to be a story that people want to listen to. It needs to be short, sweet, funny, with dramas and tension. 5 minute videos? Fuck that, who has 5 minutes? You have 1 minute - punch me in the face.

Sure, but what about all the requests from the company? Ask yourself:

  • How does it fit in MY agenda? In MY plan

  • Will it move the needle? No? Then raise it to your boss, his job is to clear your slate. Don’t do work you think will not contribute

To all managers:

People, our environment moves, it is in constant change. We have these huge fights with our work, and that is ok, that is the way it is supposed to be. This is the pattern of a video game:

Little monster 1… little monster 1… little monster 1… Big monster 1… Little monster 2… little monster 2… little monster 2… Big monster 2… little monster 3… little monster 3… little monster 3… Big monster 3

This pattern keeps the player engaged, it is fun. The pattern we need to avoid is:

Big Monster 1, Big Monster 1, Big Monster 1, Big Monster 1

How fun is that? Team, we are in the fire prevention business and not in the fire fighting business. The second pattern happens to fire fighters. We all need to understand that. We need to build processes that feed on variation, that can eat and absorb the unexpected. Most of you have been doing this for 2 years or more. Time has run out. Processes that live, move and evolve are needed. You either can build them or not. My job is to make sure we have people who can. When we don’t, the team suffers, the individual suffers, the product suffers, and the company suffers. Everyone here will have stock in the company by the end of the next two years. My job is to deliver value to both clients and stakeholders. I hope I can do this with you

Best,

Antonio

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