Writing Strategy — CEO Shoptalk

How does a new CEO write Strategy? First, she gets her mind right. Here’s how.

Big Red Car here expecting Hurricane Harvey this weekend. Likely won’t get to the ATX until Tuesday. Whoa, Nellie!

Pray for those along the Gulf Coast who will be dealing with the first hurricane to hit Texas since Ike in 2008. Governor Abbott has already designated thirty Texas coastal counties as disaster areas. The Feds are already pouring into the fray. Well played, FEMA.

So, the Big Red Car is constantly talking to CEOs about their Strategy — the Strategy for their company. It is, sometimes, a confusing and disjointed talk.

We see CEOs having no problem with Vision and Mission, but the second it turns to documenting their Strategy, things go haywire.

The objective today is to get you in the right frame of mind to write your Strategy. Not to write it, but just get into the right frame of mind to be able to write it.

What is strategy?

Remember this:

 1. Strategy belongs to the leadership and is the view from 30,000 feet which converts the Vision and Mission into action. It transforms ideas into an action plan. Action.

 2. Tactics belongs to the management and department heads. It is the view from 10,000 feet and converts Strategy into functional and departmental objectives.

 3. Objectives are assigned by management and department heads to individuals and are specific deliverables enunciated in the Tactics. Objectives are “boots on the ground.”

Objectives are SMART — specific, measurable, attainable, realistic, time constrained. [Pro tip: the attainment of objectives is the critical yardstick held up to personal performance. Your Performance Appraisal system ties into Objectives. Make this so.]


As writers and storytellers, we are all told to “write what we know” which identifies the problem — CEOs, new CEOs particularly, don’t know much about Strategy. So, they freeze up.

Let the Big Red Car help you get your mind right about writing your Strategy.

Do not “write what you know.” Write what you can imagine based on what you know.

Say to yourself, “This is just a first draft. Nobody will see it but me. I can use my imagination to fill in what I really don’t know. I know how to use the DELETE button. This is going to be fine. Here we go!”

If you do that, you will start to be in the right frame of mind to begin writing your Strategy.


In the balance between imagination and knowing, the mix will be in the order of 10:1 — meaning you will throw in ten parts of imagination for every part of precise knowledge.

This ratio is even true for serial entrepreneurs. They may be more comfortable about the challenge because they have done it before, but they are trying out a new hypothesis, so it still requires imagination.

When I talk to CEOs about crafting their Strategy, this seems to help as it empowers them to blunder forward without having to actually know the end game.


Here are some specific tips which may be helpful:

 1. Constantly repeat, “This is just a first draft and it can be revised, edited, rewritten a lot before it is finalized.” [Guess what? It will be and each time it will get better and better.]

 2. Before you begin ,grab a bunch of index cards and write out some “beats” — ideas you think will be part of the Strategy. Do not try to make them orderly; make them random and a stream of consciousness. Later, you can organize them. Writing out beats absorbs the nervous energy and feels like progress, because it is. This is a writer’s trick when they feel blocked.

 3. Listen to the voices in your head. I find the voices in my head have a lot of great ideas. Listen to them. Close you eyes and tell them, “Voices, speak up. The floor is yours.”

 4. You have to find, uncover, discover, invent your Strategy. You cannot Google it or buy it on Amazon, but you can find it, uncover it, discover it, invent it. Right now, you do not actually know your Strategy. That is why you have to write it, to discover it. It is a journey of discovery, not a tech manual.

 5. Remember that Strategy is the conversion of Vision and Mission into action. It is not a recitation of “ideas;” it is action. Sure, it’s action from 30,000 feet, but it has to move the effort in some direction. Action.

 6. You cannot know the future. Nobody can. This is why you have to imagine it. One cannot know what has never happened, but one can imagine a world in which your hypothesis, your idea works. Imagine that future.

 7. It is harder to start a story than it is to end a story. Your Vision and Mission are the end. Start at the end and walk the cat backwards to the beginning.

 8. Pick a day, time, and sit down to write. Make an hour long appointment with yourself. OK, do the prep work we’ve identified above, but commit to do it. Work for one hour and then stop. Stop when you still know what you intend to write next.

At the end of the first such appointment, make your next appointment. It will get easier and easier.

 9. You will write, revise, edit, rewrite, rewrite, rewrite, edit, rewrite until your Strategy begins  to be coherent. You are not looking, initially, for “good.” You are just looking for coherent.

Later, you will say, “Hey, this pretty damn good.” Right now, let’s just get our heads right.

 10. Do not show your Strategy to anyone until you think you are almost there. Then identify the right people — not your colleagues and not your board and not your mother. This bit of wisdom will not be used until you are finished, but I want you to think about it before you start writing so you can see where this leads.

 11. Write.


Let me give you a quick overview of how things might look at their simplest.

Imagine you are Winston Churchill and your army has just been whipped by the Germans. The lads are home from Dunkirk without their weapons and you have a begrudging respect for the ass whipping the Krauts administered on the other side of the Channel. You are sorely disappointed in your and the French army who collectively outnumbered the Germans, who outfought your boys.

You have given your “fight you on the beaches” speech and now the enormity of the challenge begins to press down on you. So, since you are a winner, you begin to map out your Vision, Mission, Strategy, Tactics, and Objectives.

Vision — a free Europe and England absent of the evil of Nazis

Mission — free Europe and England by armed assault

Strategy — rebuild the English army into a fighting force capable of defeating the Germans in open combat, invade the Continent, destroy the German army, use airpower to take the fight to their Homeland, build an alliance with those pesky Americans, put pressure on the Germans from England, Russia, North Africa, the soft underbelly

Tactics — beg the Americans for weapons, get the Americans into the war on our side, kiss FDR’s ass, reorganize the army, re-equip the army, learn from the experience in France what we have to do to beat the Germans, train the army to fight and win, bomb the snot out of German industry to preclude their supporting their own army, invade North Africa to stretch the German army to a breaking point, develop a theory and an action plan for amphibious warfare, train an officer corps which can throw off the defeatist attitude of Dunkirk

Objectives — draw up an invasion plan for landing on the Continent by date certain while identifying the minimum force level; grow the army to that level; invade North Africa to obtain experience fighting Krauts; build a fleet of landing craft capable of landing men, tanks, and artillery in large formations to ensure not being driven back into the sea; rehearse landings; appoint aggressive commanders who will attack, pursue, destroy German formations; pick a date, conduct an invasion of France; drive on to Berlin; kill Hitler

One may quibble that one or another of these things falls into some other heading, but remember they are part of a coherent whole.

Now, dear CEO, let’s just get you in the right frame of mind to start. That’s all. Say, “Hey, I can do this. My mind is right. I’m not frozen anymore. I have more imagination than Walt Disney. Here we go. Whoa, Nellie.”

And, that dear CEO, is how the cow eats the cabbage.

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car. More on this Strategy stuff in the weeks ahead. Screw you, Harvey.

  • Adam Sher

    Going through this exercise now. Late for us but not too late.

  • sigmaalgebra

    Really nice!

    Do not “write what you know.” Write what you can imagine based on what you know.

    Nice observation!

    I’ve had lots of training that, with a level of severity, e.g., to defend against criticism from picky, nasty school teachers, says be able to justify, hopefully down to the level of Zermalo-Fraenkel axiomatic set theory, everything say or write, and that training and severity truncate nearly everything about “imagine” but don’t yet solidly know.

    But, as I learned on my own, in research, to get new results, first have to guess the results and commonly along the way to imagine what might be true or false, often with just crude guesses. E.g., “Naw, likely A can’t be true; if it were, then this other stuff would be true and intuitively that’s a bit much to hope for. So, first-cut, assume A is not true.”.

    So, the actual training said don’t say anything can’t solidly support, but research experience says that imagination is crucial and has to be encouraged!

    Right, likely don’t want to show guesses or what imagine from 30,000 feet to board members, candidate hires, etc.

    And the post is good also on the other steps from vision and mission through tactics and objectives.

    Yup, after Dunkirk (26 May to 4 June 1940), poor Winnie was in deep trouble! Then right away there was the Battle of Britain, Jul 10, 1940 – Oct 31, 1940. Nice example about Winnie!

    Winnie might have looked at what Manstein thought of and how he did that.

    Yup, for Winnie, trust in the RAF, the Spitfire, and the short range of the ME-109, as at


    The Spitfire’s lower wing loading endowed it with superior maneuverability, but the Messerschmitt’s principal disadvantage lay in its limited range. After 20 to 30 minutes over the average British target, a Messerschmitt pilot would have to break off his engagement or he would run out of fuel before he could return to base across the English Channel.

    England has access to the Mideast oil, and Germany has essentially nothing in oil, has to try to take over Romania, the Caucasus, and the Mideast or make motor fuel just from coal and water — expensive. Know that the English Channel will still be there. Know that much of English industry is out of the range of German bombers. Note that Germany should not get into a two front war, was already on the way to fighting with Russia (Operation Barbarossa, 22 June – 5 December 1941) and their fight with Russia would have long supply lines and a long front while Russia has lands west to east across 11 time zones; e.g., if invaded from the West, Russia can retreat to the east of the Urals! And Russia has tanks, airplanes, oil from the Caucasus, and can have 6 million men attack at once. Try to get the US involved: As England has the English Channel, the US has the Atlantic and Pacific oceans! Note that the US “industrial capacity is awesome”.

    Okay, for strategy, and just imagining some of it,

    (1) Make my Web site so that users are intrigued, sucked in, at least curious, right away.

    (2) Make the site so that a significant fraction of early users really “love” (after YC founder Paul Graham) the site.

    (3) Have the site good enough that users can be pleasantly surprised, thrilled, intrigued, become involved, maybe addicted, have it become a new important tool and/or fun toy in their lives, eagerly tell others about the site.

    (4) Arrange that a user can easily send the best results they get to associates, friends, family.

    (5) Take the opportunity to do some unique, really effective ad targeting.

    (6) To get virality, progress for users making social connections, and a network effect have some suitable means for users sending to other users or people not yet users who will want/need to become users to process what was sent.

    (7) Have some publicity means that are surprising, original, radical, provocative, and generate huge interest, buzz, media excitement, traffic flow, advertiser interest, etc.

    (8) For a good image for the site, be explicit in publicity and in parts of the site about what the site can do for civilization, democracy, culture, professional growth, crafts, family, etc.

    Ah, since

    This is just a first draft and it can be revised, edited, rewritten a lot before it is finalized.

    that’s enough for now!

  • Love this. In particular the Exemplars section which anchors down the concepts.

  • JLM

    The first step to writing your Strategy is to get your mind right, get ready to write. Here’s how.



    #strategy #ceo #entrepreneur #founder #startup