Strategic thinking is easy; it's making the choices that's tough!

Posted by Jack Derby, Head Coach on Sat, Jul 30, 2016

At our company, we have the privilege of being the strategy guys for a large number of customers ranging in size and shape from venture-backed tech startups to colleges to resorts to large police departments to industrial manufacturers and a wide variety of service organizations.  Add to that frothy mix of markets, a variety of business structures that range from closely held families, to municipalities, public corporations and businesses that are owned by venture and PE firms, and it all becomes a wonderfully engaging puzzle of assembling future directions and the tactical building blocks to move from here to there.

business_plans-4-resized-600.pngThe really fun part of this work is doing the discovery, diving deep into the numbers and spending hours and hours of time interviewing the senior team as individuals and then guiding them as a team through the maze of creating a forward motion tactical plan that finally gets them there...wherever that is.   Entering into the very beginning of the strategic process with any of our customers, new or old, I know that, after all of the fact gathering, after all of the market and customer research, and after all of the interviewing, if neither I nor the team have the answers at the beginning, I know that the process will have a successful outcome.  

Why's that?  Very simply...

  • ...we will argue through our various points of view
  • ...we will work harder to think very differently and get out of the day-to-week-to-monthly rut
  • ...we will leave behind our inhibitions about not wanting to make fundamental change 
  • ...we will focus more intently on the real value that we need to bring to our customers
  • ...we will visualize five years out, and we will think and plan for 18 and 24 months from now
  • ...and, most importantly, we will force ourselves to make choices.  

Eisenhower on the eve of the invasion of Normandy stated... "In preparing for battle I have always found that plans are useless, but planning is indispensable", and I would somewhat agree.

Frequently, in our strategic sessions, I see the very positive impact of just the act of bringing the senior team together into a formal planning process as one of the primary benefits in itself.   But I would modify and then extend Eisenhower's comment to... "In preparing for business strategy, I have often found that plans are useless, but planning is indispensable", but the absolute primary benefit is having the team make unified choices.

Not making strategic choices is like playing tennis without a net.  It's like having a sales manager just push for numbers without first making the tough decisions on the fundamental sales models and territories. It's like marketing any product without making firm decisions as to exactly what the inbound/outbound balance will be. Bottom line for being successful in business is that we absolutely need to make the tough strategic choices.  

business_plans-6-resized-600.jpgThis weekend, as we end the first month of this critical third quarter, and we tally the numbers as to where we are in the game, I would ask you to take an hour or so and at least write down the strategic choices that we now face between the beginning of August and the end of the year.

  • Getting the choices down is the first step.  Don't try to get to the answers, just detail the choices
  • Synthesize those with the larger team next week, and agree on the priorities and the timing
  • Schedule offsite time in late August and go through whatever strategic process you are using

 ...and then push everyone on the team to make the tough choices, both individually and then as a team. This is not consensus building, but full and openly stated total agreements.  You absolutely must ask for and hear an "Amen" from everyone as to the choices being made.  

If you want a few ideas as to how to conduct your strategy processes, you can just reach out to Jack at and get free advice, or you might want to click on to any of the following:


hillarydonald.jpgOne more critical choice-Hillary or Donald?

On another note, as I think about choices, it occurs to me that we still have about 90 days to think the tough choices of either Hillary or Donald.  Like you, I've talked to hundreds and hundreds of people about the candidates.  Not one sales meeting or strategic offsite that we're involved in now goes by without "the discussion".  For some, it's an easy choice, while for others, they've told me that they simply are not going to vote, or worse, they plan to write in either Bernie or Cruz- two embarrassing non-choices.  

My only request is to ask you to spread the word to your friends and associates to make sure that they go to the polling booth and do not waste their vote.  In business, in politics, and in life, making the choice is always the most difficult, but also the most important thing that we can do. The outcome of this critical choice is that we must move ahead!

Have a superb weekend!  


Whiteboarding_2-1.jpgYou may want to think about working through a half day "Whiteboarding Session" with us now that you're deep into Q3.

Similar to six month and annual health checkup, in a highly interactive four or five hours, we'll take everything apart and put it back together again probing, questioning, listening and pushing just a bit in order to provide you with an immediate assessment of what we see along with a number of immediate recommendations.

Depending on your focus, we can look at the company as a whole strategically or financially, or take a much more specific view into the inner workings of your sales and marketing departments.


  Jack Derby
Head Coach  

 Derby Management...for 25 years
 -Sales & Marketing Productivity Experts
 -Business & Strategy Planning Specialists
 -Senior Management Coaches for CEOs & VPs

 Box 171322, Boston, MA 02117
 Jack's Cell: 617-504-4222 

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Tags: Making Tough Choices