Daniel

In this post, I’m sharing the learning map that I’m using to acquire a strong coaching skill set.

After some deliberation, I decided to pursue the first year as a self-guided learning project instead of getting formal credentials. To set myself up for success, I wanted to get clear at the outset on my motivation to learn, the abilities and knowledge required, as well as the best methods for getting there. Here’s the learning map that I’ve drawn and continue to update along the way.

Reflecting on my first year as a coach, I realized that now was a good time to go through formal coach training. At that point, I had done more than 200 individual coaching sessions and reached product/market fit while still being in the early stages of my development as a coach, where I suspected that training might have the biggest impact. I enrolled in a 6-month program with David B. Peterson, Google’s Director of Executive Coaching and Leadership where I got access to world-class teachings and a community of peers who are significantly more experienced than me.

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For more context on learning maps, I recommend picking up the book “Ultralearning” by Scott H. Young.

Giving others feedback is critical to help them succeed. It’s also really difficult, both for the giver and the receiver. Here are some pointers on how to do well in both roles.

How to give feedback

• Goal: Provide outside perspective and encourage effective future behaviour.
• Step 1: Permission. Ask the Receiver whether you can give them some feedback. This increases the likelihood they’ll change their behaviour. Honour a “no” response. If it’s clearly important, at least give them the choice for when to receive feedback.
  • “Hey, can I give you some feedback?”
  • “When would be a good time for me to give you some feedback?”
• Step 2: Behaviour. Tell the Receiver what they did well or what they did that you would like them to change.
  • “When you (insert behaviour)…” – focus on behaviour, not character
• Step 3: Consequences. State the impact that the behaviour has had.
  • “Here’s what happens: (insert consequences)”
• Step 4: Future. Either ask for a change in behaviour or say thank you for behaviour that you want to encourage. Let the receiver come up with the answer themselves to increase their commitment.
  • “How could you change that?”
  • “Can you do that differently?”
• Step 5: Validation of who people are and of their value to the organization. Also, acknowledge their openness to feedback. It’s possible to do this naturally without sounding too artificial.
  • “It’s great that you took on this assignment. You helped us make rapid progress towards X goal.”
  • “Awesome, thanks a lot!”

When to give feedback

• Ideally, give feedback immediately after you notice the behaviour because the memory will be fresh.
• Solve problems early. Don’t wait until there’s a pattern.
• Pause and reflect before giving feedback:
  • Are you angry? Are you assuming bad intent? If so, hold off for now.
  • Do you want to punish? If so, hold off for now.
  • Can you deliver it with a smile on your face?
  • Should you ask more clarifying questions first?

How to receive feedback

• Be proactive about soliciting feedback so you know how you’re doing and how you could do better. A simple question you can ask is: “How can I do better?”
• How you respond to feedback determines whether you receive more in the future.
• Take the first fall: The best way to do that besides giving great feedback is volunteering to take some as well.
• Pause and ride the immediate wave of defensiveness.
• Move from “that’s wrong” to “tell me more.” Listen carefully. Ask clarifying questions.
• Thank the person for taking the time to help you. Encourage them to keep doing this in the future.
• If you don’t like the way they give feedback, tell them later in a careful way.
• Cultivate a growth identity to respond better to feedback:
  • Love your mistakes. They are your best opportunity to learn and improve.
  • Don’t worry about looking good. Worry about achieving your goal.

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If you’d like to explore these ideas further, here are a few resources that you’ll find useful:

• The Effective Manager – Mark Horstman
• Nonviolent Communication – Marshall B. Rosenberg
• HBR archive on giving feedback – Harvard Business Review
• Stop Softening Tough Feedback – Harvard Business Review
• How Emotionally Intelligent People Give Negative Feedback – Inc.
• How to Provide Great Feedback When You’re Not In Charge – Farnam Street
• Giving and Receiving Feedback – Max Daniel

Cultivating a list of “life principles” can help you discover what you want and how you can align your actions with your values. It enables you to bring your unseen and unquestioned perspectives and ways of being into the open where you can critically examine and change them.

I started working on my own list of life principles in my late teenage years because I noticed a tendency to get washed away by the currents of everyday life. Instead of worrying about what other people thought and what the environment demanded of me, I began to pay closer attention to what I believed and valued. Increasingly, I saw every book and every conversation as an opportunity to gain clarity about my thinking.

However, there was still a large gap between my values and my day-to-day decisions and actions. Cultivating a list of life principles and reviewing them once every week or two helped me narrow that gap. The fact that this list changed a lot over time helped me appreciate that there was probably no point at which I’d have figured it all out, but that I was going to remain a work-in-progress. I’m sharing the current list below.

Looking back, I notice how critical this practice of self-authorship was to my learning and growth in my twenties. It helped me lean into my ambition, cultivate a growth mindset, and become a more effective leader and a better friend, among many things.

And yet, I used to keep this list to myself and not tell anyone about it out of fear of being judged, expecting that others might not be able to appreciate this rather unconventional practice. At this point, I feel comfortable sharing myself more openly, which prompted me to write this post. At the same time, I’ve also become more realistic about the idea of life principles itself, appreciating that life isn’t black or white and that no set of principles will ever do it justice. With that in mind, here’s the list.

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It’s time to stop being vague. If you wish to be an extraordinary person, if you wish to be wise, then you should explicitly identify the kind of person you aspire to become.

Epictetus

Thinking

1. Awareness
   • Pause and attend.
   • Notice that everything is simply appearing.
   • Relax in the midst of struggle and unsatisfactoriness.
   • The quality of your attention determines the quality of your life.
2. Acceptance
   • Dwell in reality and don’t argue with it.
   • Relinquish your reaction to experience by simply noticing it.
   • Your experience in this moment is good enough.
   • Don’t wish to be fulfilled. Instead, welcome all things.
3. Perspective
   • Begin again in each moment.
   • Step away and look at the situation from above.
   • Focus on what you can control. Embrace what you can’t control.
   • It’s not external events that upset you, but your judgment of them.
4. Ego
   • You are nowhere. There are no bounds between you and the world.
   • You are not your feelings, thoughts, and other contents of consciousness.
   • Ignore the crowd. Improve your life in relation to yourself, not others.
   • Keep your identity small.
5. Attachment
   • Everything is impermanent. There’s nothing to hold on to.
   • Don’t cling to ideas. Keep your mind open to what is.
   • Let go of the results of your actions.
   • You are entitled to nothing.
6. Gratitude
   • Enjoy this moment where your consciousness is bright.
   • You will die soon. Let this teach you how to live fully.
   • Compare downwards to feel how lucky you are.
   • Marvel at the universe.
7. Fear
   • Trust in your ability to handle whatever comes your way.
   • Own your fear and lean just beyond it, in every aspect of your life.
   • Choose to be excited rather than afraid.
   • Your life shrinks or expands in proportion to your courage.

Action

1. Resolution
   • Your mission is your priority.
   • Dedicate yourself to excellence.
   • Always have a challenge.
   • Every action is a vote for who you want to be.
2. Ownership
   • Act for the well-being of the whole world.
   • You have to find a way to help yourself.
   • Pain plus reflection equals progress.
   • Take responsibility for your feelings and needs.
3. Resilience
   • Treat setbacks as a test to your ingenuity and resourcefulness.
   • Don’t cling to your comfort.
   • Diversify in everything. Always have a backup.
   • Do what you can, then let things take their course.
4. Adventure
   • Follow your curiosity, wherever you can find it.
   • Treat life as a series of experiments. Do what will teach you the most.
   • There’s no treasure at the end of the process. The process is the treasure.
   • See if you can enjoy this.
5. Transparency
   • In the long run, the truth comes out.
   • Unobstructed self-expression: nothing to hide, nothing to defend.
   • Align what you say with what you think and feel.
   • Seek out games where honesty is the dominant strategy.
6. Connection
   • Treat everyone as family and assume other people like you.
   • Hold space and experience the full range of feelings behind it.
   • Resist envy. Most of life isn’t zero-sum.
   • Occasionally forgive.
7. Execution
   • Action allows you to see the world for what it really is.
   • Let your actions control your emotions.
   • Ideas are worth nothing unless executed.
   • Optimism in the face of uncertainty.

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If you’d like to explore these ideas further, here are a few resources that you’ll find useful:

• Meditations – Marcus Aurelius (Gregory Hays translation)
• Tao Te Ching – Lao-Tzu (Stephen Mitchell translation)
• The Bhagavad Gita (Stephen Mitchell translation)
• Principles – Ray Dalio
• Algorithms to Live By – Brian Christian & Tom Griffiths
• How to Fight a Hydra – Josh Kaufman
• Waking Up – Sam Harris
• Take Ownership of Your Future Self – Harvard Business Review

Coming up with options is one of the critical steps in any decision-making process. Brainstorming is a useful tool to explore the options space. This post illustrates how to do it.

People who have trouble coming up with good ideas, if they’re telling you the truth, will tell you they don’t have very many bad ideas. But people who have plenty of good ideas, if they’re telling the truth, will say they have even more bad ideas. So the goal isn’t to get good ideas; the goal is to get bad ideas. Because once you get enough bad ideas, then some good ones have to show up.

Seth Godin in Tools of Titans

1. Setting the stage

Decide whether you’ll brainstorm on your own or in a group. The latter is preferable since the perspectives of several people typically produce more ideas than any individual on their own.

Next, define the problem for which you aim to generate options, and frame it as a question. Make sure the question is open-ended and provides the appropriate amount of constraint for the brainstorm. Good examples include:

• What are some questions you could ask yourself about [this problem]?
• How many ways can you think of to test [this hypothesis]?

Agree on the rules for the brainstorm. Here are some suggestions:

• Aim for quantity, not quality. Measure the success of the session by the number of options you’ve generated, not the quality of those options.
• Defer judgment. Don’t censor at this stage. Get every idea out on paper. Don’t do anything that would signal liking or disliking of any of the ideas.
• Make sure everyone feels safe to bring up any idea that comes to mind. Encourage wild ideas since they help go beyond the obvious ones.

Finally, decide how much time you’ll dedicate to the brainstorm. Start with a short session (2-4 minutes) to create some urgency, which helps overcome censoring of ideas.

2. Doing the brainstorm

Give everyone a set of post-its and a pen, set a timer, and do the brainstorm. Don’t have the facilitator collect ideas as this limits the speed of the brainstorm.

3. Evaluating the results

Once the timer goes off, collect all post-its in one place. Group similar ideas and give every unique cluster a descriptive name.

Then, vote on the ideas. Do this in silence so everyone can form their independent opinion. Use colored sticker dots to cast votes.

Identify the ideas with the most votes. Discuss their merits and decide what to do about them.

Sample questions

Below are a few questions that have helped me come up with ideas in a variety of situations. Liberally skip any question that doesn’t elicit useful thinking.

• Meta: What are some questions you could ask yourself about this topic? Add those to the list.
• What are the individual steps? Why is each step performed?
• What are the limiting steps? How can you work around them?
• What would this look like if it were easy?
• What metrics can you use to find out if you’re on track? How can you install these metrics in your digital and physical workspace?
• Where does this process need monitoring and gate-keeping?
• What are the worst things that could happen? What could go most wrong? What do you want to avoid?
• What if you did nothing at all?
• What are the second-order effects?
• What are the critical assumptions? How can you verify them?
• Where are you uncertain and expect additional information to be valuable? How can you collect this information?
• Who is an expert at this? How can you get their input?
• What’s the minimum effective dose to get the desired results?
• What would you do to achieve your goal with only 10% of current inputs?
• How can you increase the leverage of your efforts? What do you need to stop doing?
• How can you make yourself redundant?
• What if you could only subtract to solve problems?
• Would you be worried if the details were made public? If yes, why?
• What would your successor do?

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If you’d like to explore these ideas further, here are a few resources you might find useful:

• Better Brainstorming – Harvard Business Review
• Your Best Ideas Are Often Your Last Ideas – Harvard Business Review

I rely heavily on setting ambitious monthly goals for myself and the people I work with. This post provides guidance on how to set and evaluate goals. I recommend doing this on a monthly basis. Set aside 2-4 hours at the end of each month to go through the steps outlined below. Your manager should invest about 1 hour to give feedback.

Why set goals?

• Identify and focus on what’s most important.
• Motivate yourself and your employees.
• Establish accountability for certain outcomes.

Effective goals

Goal setting produces the best results when goals are:

• Aligned and important. Each goal should help the organization to deliver one of its most important objectives.
• Limited. Each employee should have no more than three to five goals for any period. Do less, then obsess.
• Ambitious. Bigger goals that create lots of value motivate us to deliver bigger results since we’re hardwired to respond to a challenge by giving more effort.
• Beyond key job responsibilities. Goals should represent major achievements rather than items from the job description or single tasks.
• Set for a short period of time. See Parkinson’s Law. If a goal will take more than three months to complete, break it down into more proximate goals. Start with monthly goals.
• Clear and specific. Describe your goal in ten words or less. Goals should start with a verb and identify a single key outcome. Ensure you can assess whether you’ve achieved, exceeded, or fallen short of the goal.

Examples:

• Identify 35 new leads and convert five into donors. (Specify a deadline if it’s not clear from the context.)
• Test three new methods for collecting credit card payments.
• Design and conduct two experiments that will help us decide how to organize catering in the future.

Goal-setting process

This section proposes a step-by-step template for how an employee and their manager can set individual goals. Involve the employee in setting goals and determining how to achieve them. This gives them a feeling of commitment and will help with accountability.

1. Develop draft goals

Employee: Use the prompts below to come up with possible goals. Aim high: What would it take to rate this period—e.g., this month—10/10? What are the big promises you can make to your organization? Don’t constrain your brainstorming by worrying about how you’d accomplish ambitious goals.

• Organizational strategy. What are the three most important objectives for your organization for the next three months? Support them with key results.
• Unit (project) strategy. Ideally, it is completely aligned with the organization’s strategy and breaks the larger strategic goals down into responsibilities for each division.
• Comments and suggestions from previous brainstorming on monthly goals.
• Comments and suggestions from previous performance reviews.
• Organizational problems and pain points. Talk to colleagues about how to improve internal processes.
• Personal development and interests.
• Key job responsibilities. They are an inspiration for what the employee should accomplish within their job.

Once you have a list of possible goals, narrow it down to the three to five goals that will create the most value for your unit and the organization.

• Eliminate trivial goals or big tasks, or combine several related tasks into one goal.
• Which goals does your organization value the most?
• Which goals will have the greatest impact on performance and profitability?
• Which goals best position our team for future success?

Manager: Draft your own set of goals for the employee. Compare the employee’s draft goals with your list and consider which are most important to your organization and department.

2. Meet to finalize goals

Employee and manager: Meet to finalize a list of three to five goals and turn them into succinct statements. Ensure each goal meets the criteria for effective goals (see above). With the list finalized, talk briefly about how the employee might accomplish each of their goals.

3. Make a plan

Employee: Flesh out each goal using the prompts below, then send it to your manager for review.

• Goal statement: What will you achieve?
• Benefits: What are the positive outcomes if you achieve this goal? How will this advance your organization, division, or team strategy?
• Measures / verifiable criteria: How will you determine if you’ve actually achieved this goal?
• Resources required: What will you need in order to complete your plan?
• Existing resources: What existing work can you build upon?
• Step-by-step plan: What are the main steps you need to take to achieve your goal? What are the immediate next steps?
• Completion date / deadline. Be aggressive and use artificial deadlines if possible.

Manager: Approve the plan, or suggest changes.

4. Regularly review the plan

Employee: Embed the plan into your review and planning routines. Regularly ask yourself “How am I making progress towards this goal?” and “What do I need to do next?” to increase the perceived urgency and importance of the goal and ensure you’ll take action.

Goal-evaluation process

Employee: After the end of the period, answer the following questions for each goal:

• What were the desired outcomes?
• What were the actual outcomes? Please reference the most important materials you’ve produced for quick accessibility.
• Was the goal achieved? If so, how was it achieved? If not, explain why not.
• What went well and why?
• What can be improved and how?
• Do you need to communicate your evaluation to anyone?

Manager: Give feedback on the goal evaluation and capture lessons.

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If you’d like to explore these ideas further, here are a few resources that you’ll find useful:

• HBR Tools: Goal Setting – Harvard Business Review
• Objectives and Key Results (OKRs) – Google re:Work
• Deliberate Once – Nate Soares
• How to Plan Your Life When the Future Is Foggy at Best – Harvard Business Review