Chapter 7: A Tool for Developing Self-Awareness

(This is part 7 in a series of posts where I document my progress through reading Becoming a Technical Leader: An Organic Problem-Solving Approach by Gerald Weinberg, answering the questions at the end of each chapter)

1. How many reasons have you thought of already for not starting a learning journal?

None, really, since the blog posts I write qualify as one.

2. If you have a journal of any other writing you did in the past, take it out and review it.

“What do you notice first? What personal changes does it measure? Are you depressed or elated that you’ve changed so much, or are you depressed or elated that you haven’t changed very much? If you don’t have any records of your own past, aren’t you sorry you can’t measure your progress?”

I tend to think whatever I did in the past sucked. Turns out that while my knowledge (especially of the “shit you know you don’t know” variety) has expanded, my writing was just as good (or bad, whichever way you want to look at it) back then. 🙂

3. Once a day for the next week, do some familiar task in the following way:

“As you do each step of the task, say to yourself (out loud if possible): ‘Now I’m doing such-and-such.’ For instance, you might say, ‘Now I’m opening the drawer to get a pair of socks. Now I’m choosing a color. Now I’m matching the one blue sock with its partner. Now I’m closing the drawer. Now I’m sitting down close to my shoes to put on my socks. Now I’m putting on my right sock.’ You may pause at any time to ask yourself questions such as, ‘Why am I putting on my right sock first?’”

I tried this on a small-scale production deployment – I kept saying what I was doing out loud, to a microphone. I was recording a log of what I was doing, and the things that affected my decision making.

The first obvious effect was that others in the office looked at me real funny. The second was the more interesting one.

Every now and then someone comes to me asking for instructions. Typically it involves a programming or sysadmin task, and I find myself unable to articulate the exact steps, or the things I do to determine my next action. Thinking out loud while doing things made that possible.

This tied in nicely with something else: I was discussing the nightmarish 17h production deployment with our CTO, and he kept asking me questions about why we made various decisions. Eventually I was forced to admit that I couldn’t remember. That prompted an idea that we should maintain a log of some sort when we do these things.

4. Which shoe – right or left – do you put on first in the morning?

“Promise yourself a five-dollar present if you can put the other one on first tomorrow. Put a note on the breakfast table so you’ll be reminded to check your bet after your shoes are on. Keep doing this until you succeed.”

(On a side note, I’m also reading through “Pragmatic Thinking and Learning – Refactor Your Wetware”, and it proposes similar exercises.)

Left. On the first day I remembered this later in the day. On another day I was already putting the first shoe on, when I caught myself. 🙂

5. What are your legs and feet doing right now?

Moving to a beat and shuffling restlessly.

6. Set some personal development goal for yourself for the coming year.

“Note in your journal your reactions as you set this goal, and note your progress toward that goal in your journal.”

I already have – I want to learn to give presentations. I’m way behind on my progress, but my first presentation is coming up in a week or so. 🙂

7. Read at least one autobiography of someone you admire.

“Note in your journal those parts that are particularly surprising to you, and those parts that move you most.”

The only autobiographic book I’ve read, and am likely to read, is Obama’s “Dreams from my Father”. While I might not personally admire Obama – I don’t have that sort of a connection to him, since he’s not “real” to me – I do admire him somewhat.

The surprising part was his addiction. I didn’t see that coming. The most moving bit was his own sense of self-worth, or lack thereof, when he was doing volunteer work.

8. As you read this book, write the answers to these questions in your journal

That might just be what I’m doing here. 🙂


Previously: Chapter 6: The Three Great Obstacles to Innovation  Next up: Chapter 8: Developing Idea Power

Chapter 6: The Three Great Obstacles to Innovation

(This is part 6 in a series of posts where I document my progress through reading Becoming a Technical Leader: An Organic Problem-Solving Approach by Gerald Weinberg, answering the questions at the end of each chapter)

1. Knowing what you had for dessert is an application of general self-awareness to the question of health.

“How aware are you of your own health and how it affects your leadership style? How do you feel right now? Take an inventory of your physical condition, and describe how it currently affects your performance as a leader.”

I’m in poor shape, although I’ve been worse. I feel tired, and I’ve got all sorts of aches and pains all over the place. On occasion, it plays merry hell with my ability to focus, and I’m sure that if I were healthier, I’d also seem happier, which would certainly have a positive effect on people around me.

2. Poor health is an obstacle to innovation and just about everything else.

“How is your long-term health affected by your career? What is your health going to be like in the future? If you have a hard time answering that question, what makes you think your health is not under your own control? What are you doing to keep it under your own control? How will it affect your career in the future?”

Stress and longer work days affect the way I eat – the more tired I am, the less likely I am to prepare a proper meal. Instead, I tend to opt for a pizza. In the future, I’m going to go for less stress and a healthier diet. Keeping that in mind might affect the choices I make, career-wise.

3. In answering the previous two questions, did you respond that your health was “no problem”?

“What does that tell you about yourself?”

No, I didn’t. It tells me I’m not fooling myself. 🙂

4. Do you know your IQ?

“Do you let other people know? Does knowing your IQ affect your ability to lead? How?”

Not accurately, but I’ve done the Mensa online test, so I’ve got a rough idea. I don’t let other people know, because I’m fairly sure it would only serve to provoke feelings of either superiority or inferiority in others, neither of which seems beneficial. It’s been quite a while since I last thought about my IQ before reading this question, so I can safely say it doesn’t affect my ability to lead in the least.

Come to think of it, I tend to assess people based on their performance, attitude, competence and suchlike, instead of any perceived ‘intelligence’.

5. Do you like to take tests?

“If you knew you were assured of doing well, would you like to take a test? What if you were assured of doing poorly? What if you had to take the test, but were never to find out how well you did? What do these questions have to do with leadership style?”

Yes, I do. If I knew I’d do perfectly, I wouldn’t bother . In every other case, I’d do it just to confirm whether the assurances would hold.

If I wouldn’t have the chance to process how well I did, I wouldn’t see the point either.

If this says anything about my leadership style, it’s that I base my work on feedback.

6. Find some multiple choice quiz and go through it in the following way:

“Instead of picking one answer, take each answer in turn and give a good reason why that could be the answer. Then give a good reason for some answer that isn’t among the choices.”

7. Next time you’re in a meeting and several ideas are brought up, apply the technique of the previous question.

“That is, make sure you give a good reason to the meeting’s participants to explain why each idea could be the solution you’re seeking. Then offer at least one more.”

Both of the questions above ask me to do something, but not report the results. Instead of posting the answers, I’m going to go with what the exercise made me think.

In the multiple choice question, I felt like I was exploring the possibilities. It was the same with the meeting, except for one detail: with the other participants, it kind of made me feel like I couldn’t actually answer the question, for a while. Eventually, I did pick an option and put my (considerable) weight behind it, though.


Previously: Chapter 5: But I Can’t Because…  Next up: Chapter 7: A Tool for Developing Self-Awareness

Chapter 4: How Leaders Develop

(This is part 4 in a series of posts where I document my progress through reading Becoming a Technical Leader: An Organic Problem-Solving Approach by Gerald Weinberg, answering the questions at the end of each chapter)

1.  Do you have some skill that you have improved over a long period of time?

“Can you plot your progress, and can you apply your methods of learning to that of learning to be a better problem-solving leader?”

I guess programming is the best I can do here. The method, so far, has mostly been solving real-world problems. Applying the same methods for learning leadership would require actually trying to be one. Sure, it’s possible. But we’ll have to wait a while to see if I’ll do that or not. Then again, the question was can you, not will you.

2. Can you describe a plateau you are now occupying?

“Are there signs that you may be approaching the ravine [the drop in skill just before a rapid rise to the next plateau]? Are you trying to stay out of the ravine, or learn what you can from tumbling in?”

I write reasonably good code, and I have a good overall grasp on the landscape of programming. However, I still haven’t managed to do anything properly with functional programming, because it’s damn hard. That’s a ravine right there. I’m actually trying to leap in, but I get tired of it fast, and eventually quit.

3. How long has it been since the last time you climbed to a new plateau?

“Are you still enjoying the feeling of being on the flat? What are you doing to get ready for the next one?”

The plateaus, ravines and sharp climbs in my progress seemed to come in two-year cycles in the beginning. I’ve been doing this for ten years, but the last time I observed a sharp increase was about four years ago. So either I’ve been on the same plateau for four years, or I’ve been paying less attention to the change.

I’m trying to study Computer Science, to brush up on the theory behind the practice. That’s my number one strategy for preparing.

4. In the course of your life, what have you learned about learning?

Learning requires intense focus, passion and a tough skin to tolerate the constant failing. It’s also a lot of work.

5. Set yourself some personal achievement that you can practice for fifteen minutes every day for a week.

“Keep a record of your progress. Next week, pick another achievement.”

I’ve been practicing the guitar riffs to HIM’s cover of Wicked Game. Now I’m going to try to sing and play at the same time. 🙂


Previously: Chapter 3: A Problem-Solving Style  Next up: Chapter 5: But I Can’t Because…

Chapter 3: A Problem-Solving Style

(This is part 3 in a series of posts where I document my progress through reading Becoming a Technical Leader: An Organic Problem-Solving Approach by Gerald Weinberg, answering the questions at the end of each chapter)

1.  Observe someone you consider a leader.

“Make a list of this person’s activities when working with others, and see how many of them fit into the categories of understanding the problem, managing the flow of ideas, and controlling the quality. Are there activities on this list that you never do? Why not?”

For this, I’m going with a project manager I used to work for. His way of working was first to get a cursory understanding of the problem. Sometimes he’d go deeper, sometimes he’d decide it was something he didn’t need to understand it thoroughly, so he’d just dish it out to the team. At that point, he would “fan the flames” for every spark of an idea anyone had, and if there was nothing, he’d try seeding the discussion with an idea of his own – sometimes a sane one, sometimes a clearly ridiculous one. Anything to keep the floodgates open. He also had a knack for figuring out ways to test our solutions. A little bit of something for every category, then.

I’d say that while I’m fairly apt at understanding problems and testing the quality of solutions, I’m not very good at encouraging ideas. In fact, I tend to either quietly think to myself or dominate the whole discussion, being more of a participant than a moderator.

2. Observe someone you don’t consider much of a leader.

“Make a list of some simple opportunities for exercising leadership that this person misses. Do you miss these same opportunities? Why?”

I know one person whose role in the team officially sets him up as a leader. Yet he would much rather delegate the day-to-day leadership to someone who is officially in a position of less responsibility. I do think I miss some opportunities just like he does – sometimes even on purpose, if I’m not feeling up to it.

Back when I was officially a “senior software engineer”, my mistakes were of a different sort. I put myself up on a pedestal, but then didn’t actually live up to that image, and didn’t really lead at all.

3. Do you ever have trouble getting people to pay attention to your ideas?

“How do you react to their ideas?”

Sometimes I see people so stuck in their particular train of thought, that they won’t actually consider any idea that doesn’t fit their mental model of the problem. It’s tolerable for a while, but if repeats often enough, I tend to flip the bozo bit on them. After that, I typically dismiss their ideas without thinking them over – not consciously, though. Sometimes I manage to catch myself in time and actually consider what they’re saying, after which I assess the idea on its own merits.

4. What techniques do you use for gaining perspective on what you are doing when you are working in a group?

“when you are working alone? How might you improve your ability to see your own actions?”

Usually, if my approach doesn’t work and I get frustrated, I launch into meta-mode, circling around the problem and my mental model of it. If I’m actively working with a group at the moment, I’m likely to fall quiet and zone out. When I’m already alone, I don’t need that extra distance. Sometimes I use instrumental music to focus. I tend to reflect on my own actions a lot afterwards, but if I’m in a particularly emotional state, I can’t view my own actions very subjectively even in meta-mode. I need to learn how to keep my cool.

5. Next time you work with a group, list all the things you do to exercise leadership.

“If you don’t have at least ten items, do the assignment again, and keep doing it until you get a list of ten things out of one activity. When you have your list, put the items into categories of understanding the problem, managing the flow of ideas, and controlling the quality. Does your style tend to favor one category over the others? Which of your actions don’t fit into any of these categories?”

This one is hard to answer now, because I’m about to leave my current team, and most everyone else is on vacation. I’ll have to come back to this one later.

6. Overall, what new actions would you need to practice to strengthen your style as a problem-solving leader?

I need to set my own need for approval aside, and instead of obsessing over being the one who solves the problem, learn to be the catalyst for it.


Previously: Chapter 2: Models of Leadership Style Next up: Chapter 4: How Leaders Develop

Chapter 2: Models of Leadership Style

(This is part 2 in a series of posts where I document my progress through reading Becoming a Technical Leader: An Organic Problem-Solving Approach by Gerald Weinberg, answering the questions at the end of each chapter)

This chapter develops a model for discussing an environment for leadership. The model has three parts: Motivation, Organization and Ideas, abbreviated MOI.

[Edit: I missed one question when I typed these up. The missing question was number 5, and what I posted as question 5 is now question 6]

1. How would you characterize yourself in MOI terms?

“What were you like five years ago?”

Currently I’d say I’m highly motivated and fairly well stocked in ideas. In the last five years, the biggest change has been in the idea department, as I’ve gathered experience, read up on new ideas and tried them out. My motivation has been fairly high all the time, and stable at that. I’ve never been very organized, ever. I’ve even tried a bunch of ways for keeping organized. Some of them even worked (for example, making a daily list of things to do). I tend to abandon them after a run of success, though, after which the inevitable decline happens.

2. How much are you willing to do to change your MOI profile?

“What specific actions do you have planned for the next five years? next year? next month? tomorrow? today?”

The previous answer highlights one of the things I know to be my, let’s say *cough* less strong aspects. I don’t really feel much of a need to change the M axis, and the I axis is covered in my constant push for learning. However, the O axis clearly needs work.

I’m willing to give almost any sane method a try. It doesn’t make sense to try fixing this problem on the very long term, but evidently the short term isn’t right either. Perhaps a month of practice coupled with weekly notes on how well things worked would be a good start.

3. Can you think of specific events that triggered an agreeable change in your MOI profile?

“Do these events have anything in common? What can you do to increase the frequency of such events?”

The last clear milestone I can think of was when I began to have a kind of focus in learning. It was approximately five years ago, when I realized I couldn’t expect my co-workers or bosses to tell me how things should be done. The previous one was triggered by uncertainty of my own proficiency at work. The events are almost polar opposites, but both drove my motivation which in turn helped me stock up on ideas.

The best way to drive this sort of change is likely actively going outside my comfort zone.

4. Do you have a different MOI profile at work than you have in your life outside of work?

“What does this tell you about yourself?”

I think the differences are negligible. I very much identify with my professional persona, for better and for worse, which is probably the main cause for the similarity. One interesting difference is that outside work, I’m more comfortable taking a leadership position and being a catalyst, possibly due to the less severe responsibilities involved.

5. Is your current leadership style contributing to your happiness?

“to the happiness of the people around you? to making the world a better place for everyone?”

Outside work, yes. At work, a little less, maybe. I don’t think I have a significant contribution in making the world a better place, but just like you can die from a thousand paper cuts, a thousand tiny little things that are better make up for one bigger thing. In that sense, yes.

6. At the moment, does your principal motivation for change come from promise of reward of fear of punishment?

“Is this the best mode for you? If not, what can you do to get more of the other kind? How about some other kind of motivation entirely, such as an increased sense of self-worth?”

I could have chosen to stay where I am now, as I am now, and gain rewards for that. On the other hand, trying to step outside the bounds of what I usually do is, at least in my mind, more risk-prone, and as such, more likely to result in ‘punishment’. Therefore I’d say neither of the two apply. Instead, an increased sense of self-worth is a fitting description for my motivation for change in general, not just this particular exercise in changing.


Previously: Chapter 1: What is Leadership, anyway? Next up: Chapter 3: A Problem-Solving Style

Chapter 1: What is Leadership, anyway?

(This is part 1 in a series of posts where I document my progress through reading Becoming a Technical Leader: An Organic Problem-Solving Approach by Gerald Weinberg, answering the questions at the end of each chapter)

1. Observe someone you consider a leader.

“How is this person’s life different from yours? Which of these differences are a result of being a leader? Which of them are a cause of being a leader?”

The first three times I read this question, I tried to search my memories for true leadership from my own work history. Then I realized that my perspective is far too narrow.

I have an old friend who is a natural leader. He was clearly the alpha, but for the most part, he also made a point of caring about people around him. Back in the day I’d disagree with him over a lot of things, yet happily follow him most of the time. I think he also has a narcissistic streak – at the very least, from time to time he would obviously put his own agenda or ego before everything else. But then, he’d also be brutally honest about that side in his personality, which made it tolerable.

From what I hear, he has things pretty well in order these days. Family, kids, whatnot, whereas I’m still figuring out what and who I want to be. I think he’s always had an inner vision of what life for him should be. The differences between me and him are probably mostly the cause, not the effect, of him being a leader.

2. How would you expect your life to be better if you increased your leadership skills?

“Which of these improvements will arise from your changed behavior, and which from recognition of the changed behavior from other people?”

Increased confidence, I think, primarily. A self-image that isn’t in constant flux. This answer may be a bit misleading in that I don’t expect that to happen as a result of the things I need to change. Rather, that is the first thing that I need to change. If recognition from others will drive positive things, it will probably be a sort of a feedback loop. I don’t think any good change can come entirely from the outside.

3. How would your life change for the worse if your leadership skills increased?

“Will these changes be worth the rewards? How can you change, yet behave in such a way that these changes do not affect you so adversely?”

I tend to fluctuate between bouts of really low self-esteem and feeling like I’m the most important person in the world. Now, if the change improves my self-esteem, I’ll probably have a hard time keeping my ego in check. I’m hoping I can avoid the worst by keeping a keen eye on the mirror.

4. Make a list of situations in which your presence seems to increase the productivity of others.

“Alongside this list, identify situations in which your presence seems to decrease the productivity. How can you characterize the differences between these situations? (Fore example, increases in productivity might involve working with people you know well, or working on a problem that is new and different. Or perhaps just the reverse is true for you.) What do these lists tell you about yourself and the environments that empower you?”


  • When I’m the most experienced programmer on the team
  • When I’m allowed to work as a free agent, researching the issues that are giving others grief.


  • When I’m the other party to a personality conflict. Arguing with someone instead of arguing for a case is very tiring. It drains me, and I’m sure it drains others as well.
  • When I manage to sidetrack another person, or even the whole team.

I tend to carve myself a niche where I get the warm glow of appreciation from people. Typically I stay well within my comfort zone, which is sort of a bummer, growth-wise.

5. Based on the two lists from the previous question, are you statistically an asset to groups, or a liability?

“Do you seek out situations in which your leadership will be positive, or do you more often look for situations in which you can learn to do better? Do you, in fact, learn from these situations, or do you just keep repeating yourself?”

I think I’m a net benefit, but then if I didn’t, I wouldn’t be writing this, I guess.

A lot of the time it seems like projects start out promising really interesting learning opportunities, but end up being a bunch of boring grinding. Whether that’s due to unrealistic expectations, or learning the lessons quickly, or merely me being fickle is really hard to say – the jury is still out on that. Still, I feel like I’ve learned something on every project I’ve been on.


Next up: Chapter 2: Models of Leadership Style.

Becoming a Technical Leader

(… in several really really difficult steps.)

A day before Christmas Eve the postman was kind enough to bring me a copy of The Deadline and Becoming a Technical Leader: An Organic Problem-Solving Approach. I read them both in two days. Such a quick read does neither of them justice, but it’s particularly not suited for Becoming a Technical Leader, which is more of a “getting to know yourself” work book than it is a how-to-manual.

The book is divided into five parts, each dividing a particular theme into chapters. At the end of each chapter is a list of questions for the reader. The book suggests that the reader keep a journal of things learned (an idea neatly mirrored by the protagonist in The Deadline). Among the things to document in this journal would be written answers to each question.

I thought I’d give the book another read, and this time, pause after each chapter to write down my answers to each of the questions, and perhaps learn something in the process. I’m going to post each chapter’s questions and answers as an individual post, and link them all back here when I’m done.