To Get to the Point, you need to Know the Point

It sometimes feels like you need lots of words/pages/slides to look/sound credible, but great communicators go through the hard work of refining their idea/message/recommendation down to a crisp, easy-to-digest message.

“I didn’t have time to write you a short letter, so I wrote you a long one” – Mark Twain

This concept is so valuable in so many ways — for example:

  • Getting to the root cause of an issue requires that you continue to ask “Why did this happen?” to get past the symptom/second-order effects, and get to the root (see 5 Why’s Technique)
  • In Product Management, it’s tempting to add many variations/options/different products, but it’s powerful when someone works on refining that down, like the classic story of Steve Jobs in 1997, created a simple grid with 4 product categories and shifted Apple to only make 1 product in each category, with a focus on excellence
  • When communicating with others, push yourself to try to get to the point faster — the US Military communicates very efficiently in this way, often using things like a Bottom Line Up Front (BLUF) or Executive Summaries (not to be confused with Introductions) to rapidly communicate the point, instead
  • When launching a new IT project, don’t rush through exercises like a project charter or determining the business case/justification/problem (see Digital Services Playbook, Play #1) — invest time in peeling back the layers of really understanding what the real problem you’re solving is — it will be well worth it!
  • Amazon has a meeting culture where the meeting requester/leader crafts a 6 page memo with the recommendations/context, and everyone in the meeting silently reads the memo to start the meeting.  The quote below shows their approach and their expectation that a good 6-page memo should take a week or more to develop and refine into a high-quality product.

We don’t do PowerPoint (or any other slide-oriented) presentations at Amazon. Instead, we write narratively structured six-page memos. We silently read one at the beginning of each meeting in a kind of “study hall.” Not surprisingly, the quality of these memos varies widely. Some have the clarity of angels singing. They are brilliant and thoughtful and set up the meeting for high-quality discussion. Sometimes they come in at the other end of the spectrum.

In the handstand example, it’s pretty straightforward to recognize high standards. It wouldn’t be difficult to lay out in detail the requirements of a well-executed handstand, and then you’re either doing it or you’re not. The writing example is very different. The difference between a great memo and an average one is much squishier. It would be extremely hard to write down the detailed requirements that make up a great memo. Nevertheless, I find that much of the time, readers react to great memos very similarly. They know it when they see it. The standard is there, and it is real, even if it’s not easily describable.

Here’s what we’ve figured out. Often, when a memo isn’t great, it’s not the writer’s inability to recognize the high standard, but instead a wrong expectation on scope: they mistakenly believe a high-standards, six-page memo can be written in one or two days or even a few hours, when really it might take a week or more! They’re trying to perfect a handstand in just two weeks, and we’re not coaching them right. The great memos are written and re-written, shared with colleagues who are asked to improve the work, set aside for a couple of days, and then edited again with a fresh mind. They simply can’t be done in a day or two. The key point here is that you can improve results through the simple act of teaching scope – that a great memo probably should take a week or more.

Jeff Bezos, Amazon Shareholders Letter

You’re Not Good at Multitasking

In computer science, the concept of a computer’s processor switching from one system to another is referred to as context switching, where the computer switches from updating your gmail browser page over to your Microsoft Word application, etc.  Computers are very good at this, but people are horrible at this.

Everyone, myself included, thinks we’re great multi-taskers who are great at juggling lots of things at once, and we’re so much faster doing that than stopping to focus on one thing at a time.  While this sounds intuitive, it’s usually horribly wrong.  Not only are you slower overall when juggling lots of different things, you also can’t significantly advance the important/complex work — instead you’re often attracted to, and only make progress in, tactical/shallow work.

Cal Newport, a professor at Georgetown, has written a great book (Deep Work) on this concept of how important/valuable work happens when you ignore everything else, you don’t check Facebook every 6 minutes, and you instead really focus on the important, complex work that is valuable.  A similar book I’ve heard great things about is Nicholas Carr’s The Shallows.

There are techniques that can help in this vein, like the Pomodoro Technique, where you intensely focus on a single task for 25 minutes, take a 5 minute break, repeat that cycle 3 more times, and then take a half-hour break.

Another concept is to check your email only a few times a day (2-3 times), and intensely review/groom/action your inbox during these times, instead of checking in on it every few minutes, you’ll be much faster.

Paul’s Graham wrote a great essay, Maker’s Schedule, Manager’s Schedule, about the difference between the work schedule of makers (e.g. software developers, business analysts) and managers (leaders who are focused on making decisions through a series of reviews and meetings), which is related to this concept that if you’re a maker, you need to dedicate significant blocks of time to advancing important/complex things.

Not only is focusing on one things overall faster, it can also be a much more effective way to deliver value more frequently — instead of slowly advancing 10 big initiatives, if you finish 1 before moving to the first, it means that first thing got complete and delivered value faster, which is great (one of Agile’s great values is encouraging/forcing people/teams to actually prioritize their work and then force prioritized progress within timeboxes — check out Great Big Agile by Jeff Dalton for some great techniques for this within a team/organization context).

It’s hard to do in today’s frenetic, distracted world; but when you can carve out intensely focused time, you’ll accomplish important things much faster than you would trying to advance everything all at once.

(James Hance is an awesome artist, who does amazing mashups.  This one, The Meep is a great mashup of Edvard Munch’s 1910 The Scream and Beaker from the Muppets — you can buy a print of The Meep at

It’s Tempting, but DO NOT skip Planning and Premortem

So many leaders or teams quickly move too quickly (or skip entirely) the early parts of a new project/initiative, failing to invest real time in wrestling with questions like:

  • Should we do this project? (This question is skipped way too often — think about investing in exercises like a business case or a project charter to ensure everyone is clear on the value/ROI)
  • Who are all the stakeholders/users (not just the primary one(s)) who are affected or will be affected by this project? What do they really want/need?  What are their pain points?  What are their issues they don’t even know they have?  (Note: The whole field of User Experience (UX) and User Centered Design (UCD) has many, many tools and techniques to help navigate this area)
  • Do we really understand why we’re doing this project? (What is the business problem?  What value will the ‘business’ receive at the end of the project?
  • Do we understand the different ways we could break down the value we’re going to deliver, to understand the trade-offs in different ways to approach the project (e.g. could we deliver value earlier and get validation (reduce risk) by starting to focus on a specific Minimal Viable Product instead of running in the direction we think is ‘most efficient’ for the final product (which almost certainly isn’t the most efficient way, because there’s so much we don’t know at this point) (See The Startup Way by Eric Ries)

After we get through those phases, we should avoid the desire to jump into execution by taking a breath and asking ourselves:

  • Conduct a Premortem (see HBR Premortem article):  Get the team together and ask everyone to imagine this project has failed spectacularly — start writing down, independently, all the ways it failed, and then have the group discuss (Heard about this from Seth Godin)

Clayton Christensen, in his book How Will Your Measure Your Life? encourages people to ask a great question early on in a new project/initiative:

What assumptions must prove true for this plan to work?

New Top Career Book Recommendation

When I’ve chatted with people in the past about how to plan/manage their careers, I would often to refer to the book What Color is Your Parachute as my go-to recommendation, as it’s packed with great resources (a great friend of mine referred me to its Flower Exercise many years ago).  But recently I’ve been listening to Clayton Christensen’s (who recently passed away) How Will You Measure Your Life? (Harvard Business Review has an article about the book here), and it’s now going to be at the top of the list, along with What Color is Your Parachute as a recommendation for people to invest the time in reading.

Christensen is famous as an Harvard Business School profession who wrote extensively about disruption, and I’ve enjoyed his writings on that topic; but this book is a great read in a very different direction.  This book is focused on asking great questions about how to plan and run your life, with a focus on how to measure ‘success.’

He starts the book talking about how interesting it was to see at school reunions how different people’s lives evolves, and how they prioritizes their time and energy.

He shared some great concepts to be thinking about through your career like:

  • Deliberate vs. Emergent Strategies: The different between having a clear goal and working toward it vs. being open to new opportunities and seeing where they take you
  • Identify Assumptions: Before making a big decision, thinking about ‘What would have to be true for this to success?’, where you invest time in thinking about what assumptions/dependencies are inherent in this thing you’re considering (similar to investing time in a pre-mortem)
  • Resource Allocation: How will you invest your time and energy?  Be careful not to invest it only where short-term feedback/gains show up (such as work) and not invest where it takes a while to see feedback/gains (e.g. relationships with your spouse, children, friends)

I’m only 40% through the book, but it’s already so good I have to share it.

Moving up the Value Curve

A mentor, and family friend, of mine made a great point to me years ago. He explained that people are valued (e.g. job security) and compensated based on the value that they offer their organization (that part should be obvious), and a common way to increase the value you deliver is to manage/oversee increasingly important parts of the organization.

He explained that people often start their careers managing things (e.g. technology, machines, clothes on a retail floor). To become more valuable to your employer, you should look to manage people (e.g. overseeing, supervising, leading), and then manage money (e.g. budgets, purchase/investment decisions, a profit & loss center).

If you want to increase your value, you want to be moving toward a role where you’re leading/influencing a large number of people (every organization is different — maybe that’s a Product Manager in your organization, or a second-line supervisor) and/or overseeing a large budget/revenue area, such as a P&L Owner (Operations Division Director), etc.

Update: An interesting point a colleague recently mentioned to me, after seeing this post, was thinking about how innovation/disruption fits into this.  People who make improvements into process and/or innovation (e.g. improving how an organization delivers service, or improving an internal process to increase efficiency) is another way you can increase the amount of value you create, which is a great point!

How to Pick a Real Estate Agent

Some (unsolicited) advice if you’re looking to pick a real estate agent:

  • Don’t pick the first real estate agent you hear about, meet, or get referred to! It’s an important decision for a huge financial transaction, so it’s well worth your time to consider what you’re looking for in your agent
  • Check out Ramit Sethi’s (great financial blogger) blog posts about buying a house — this is a huge investment, so take the time to read up on how to do this well, as saving some money/avoiding headaches here is so much more valuable than reducing your Starbucks monthly costs

We went so far as to ask several of our friends for real estate agent referrals, emailed them a list of questions (see below), reviewed the answers, and then selected a few of them to meet in-person to “interview’ them before we picked one — it took some time, but we felt like this was one of those decisions in life that was worth it (we ended up with a great agent, in case anyone wants a referral for someone in the Northern Virginia area).  Here are some questions you could ask a potential real estate agent:

  1. What percentage of your clients are buyers (vs. sellers)?
  2. Which cities/neighborhoods do you primarily represent buyers and sellers?
  3. How many buyers did you represent last year?
  4. What’s the average difference (in dollars and %) between your initial offer and final sale price, when representing buyers?
  5. What is your business philosophy? (How do you search for new homes? How many homes do you show a buyer each outing? Are you able to show houses on nights and weekends?)
  6. Will I be working with you directly or others as well? In other words, will you handle all aspects of my transaction or will you delegate some tasks to a sales associate or administrative assistant? A knowledgeable assistant can be invaluable, but you want to make sure you can connect with your agent regularly.
  7. Will you represent me exclusively or may you choose to represent the seller?
  8. Do you work full-time or part-time as a real estate agent?
  9. How many other buyers are you representing now? How many sellers?
  10. Is your real estate license in good standing?
  11. How many years of real estate experience do you have?
  12. Are you also a broker,  Realtor, and/or an agent?
  13. If we sign a buying agreement with you and it isn’t working, what is your policy about cancelling an agreement?
  14. What are the top 2-3 things that separate you from other realtors or real estate agents?
  15.  Can you provide me with the names and phone numbers of 1-3 past clients who have agreed to be references?
  16. What haven’t we asked that we should?

What Great Leaders Look Like according to Bill Campbell

Trillion Dollar Coach is a great read (or listen if you’re an audiobook fan like me) about Bill Campbell, a football coach who pivoted mid-career into a business executive in Silicon Valley, as an executive at Apple, a CEO of Intuit, and an executive coach to Steve Jobs and other high profile leaders.  The book talks about some the qualities he looked for in leaders, which I found very useful to consider as I think about how what I look for when I’m interviewing or considering someone for creased responsibility:

  • Smarts:  Ability to learn quickly and apply new concepts in novel ways
  • Hearts:  Ability to empathize with and understand others
  • Grit:  Ability and willingness to work hard
  • Curiosity:  Desire and openness to continually learn (Avoid people who “have it all figured out” — instead you want people who always have more questions)
  • Winning Right:  A desire to win the right way, with a team-first attitude and integrity, all the time not just when it’s easy
  • Humility:  Pay attention when people celebrate other teams or leaders succeeding, not just themselves
  • Sacrifice:  Pay attention when people are willing to sacrifice something for the organization, another team, or a customer


Replace recurring chaos with a RAM

Most teams have a lot of recurring tasks they have to keep track of, such as an HR team doing annual benefits ‘open enrollment’, or an IT Service Desk team reviewing weekly automated backup status messages, or an Accounting team doing their monthly book close, or that annual data audit people always forget to do.

Many teams remember those types of tasks in the heads of different people on the team. Some have recurring Outlook/G Suite calendar reminders.  Some have sticky notes.  Or smartphone alarms.  But all those approaches are prone to lots of issues (e.g. someone is sick on a key day, or someone leaves the organization and doesn’t transfer that knowledge well to new team members).

I’ve seen a lot of value in creating a centralized Recurring Activity Matrix (RAM), which can be a simple table in a wiki tool (e.g. Microsoft SharePoint, Atlassian Confluence) where a team can see what recurring activities exist, their frequency, and what procedure/checklist goes with that task.

I’ve found a great, simple, cheap approach is to publish that table and then create an automated, email reminder for each row using SendRecurring, which is a free or cheap service (depending on how many tasks you juggle) to send emails as a reminder, ideally to a system to ingest and publish them to the group, such as Atlassian Jira Service Desk (JSD).

Just creating this simple knowledge management tool and incrementally refining it, each time you identify something the group should know about it, is a great way to improve the operational resilience of a group, and drive people to identify the work they do (and ideally create procedures/checklists/processes to define them).

A RAM table could have columns like this:

  • Owning Team (if your organization has more than 1 team in it)
  • Task Name
  • Associated Task Procedure/Checklist (e.g. maybe a link to a wiki-based checklist or a formal process asset that defines the procedure)
  • Frequency (e.g. Weekly)
  • Trigger Day/Time (e.g. 28th of each month at 11am EST)

(I’ve written about this before, but I think it warrants another post because it can be so valuable for teams to do)

Maturity-based Management

It sounds obvious, but as a leader, it’s critical to manage a team based on the team’s current maturity level.  For example, if you have a high-maturity, high-performing team stacked with A+ players who know how to do their roles well, are excellent at the needed hard skills, and collaborate as a team incredibly well; you should not treat them like 5 year olds playing soccer. Conversely, you should not treat 5 year olds playing soccer like a high performing team (e.g. explained nuanced optimization concepts, when they’re still struggling with the fundamentals).

This sounds obvious, but often people try to focus on team performance metrics, such as Scrum team velocity or first-call resolution, when they should realize the team needs a lot of work on the fundamentals (e.g. ensuring the team understands their purpose and context within the organization, understanding why various meetings are held, clarifying expectations of speed vs. quality).

Don’t Keep Doing What You’re Doing when it’s Crazy

If you’re ever in an environment as a leader where things are crazy-chaotic, and it feels like all you do is play whack-a-mole, constantly putting out fires (issues) reactively and you’re not advancing any of your priorities, you need to do something that will feel counter-intuitive.  You need to stop focusing on all the crises (just for a few moments), and start to build a plan to build a stable foundation for your team to work on.
Think about things like how to establish some fundamental key processes/procedures/checklists, how to create some quality checks so you’re not constantly auditing and cleaning up bad data, and how you can really move the needle on:
  1. People (e.g. Do you need training?  Do you need to change the roles certain people have on the team?)
  2. Process (e.g. Do you have an approach to where you publish knowledge and how you’re sharing with your team to start to become more consistent and efficient?)
    • Think about writing down procedures/guidance for your most common procedures, and incrementally improving the consistency and quality of those, while you work on covering more and more of your team’s work with some type of framework
    • Or maybe the work is difficult to codify, and instead you should look at something like Agile Scrum to provide a framework to discuss/analyze/validate the ambiguity of the work and incrementally advance and validate the work
  3. Tools (e.g. Do you need to invest in collaboration, workflow, or other tools?)
Leadership: get out of whack-a-mole / crisis management and build a foundation of stability (people, process, tools)