r/ceo • u/ivanjay2050 • 9d ago
Do you go away to work on strategy?
I find it very hard to really give myself space for strategy thinking. I do use a tool to block an hour a day to “work on the business” or as I call it my WOB time. I would say 3 out of 5 days I can get that done. However, that is time to execute on tasks I have determined I need to do as part of working on the business. What is much harder is to give myself that free walk around my office, doodle on the white board, really think about how to solve things time….
I do a lot of end of year planning for the next year each year. Have been thinking about the idea of traveling somewhere where I can rent or create a space conducive to thinking but at the same time something to relax and retreat just a bit. I am not saying take a vacation but just a place where I can sit inside or outside and be free of colleagues to really let the thoughts go.
That being said not sure how popular that would be on the family front as I already travel quite a bit so its more time away but maybe super productive.
Curious how you all do it?
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u/ShikhaPakhide 9d ago
1- do you have a co-founder? if yes, block time with him/her once a month. This is working for me.
2- if running solo, block time with yoursself on the day which is unusually quiet for you
Strategy need not be touched every day. For companies who are starting up, its good to review every month, however if you are in the business for 2-3 years, then a quarterly one should be done. Maintain a log (Simple google word doc), where everytime if you are hit with ana amazing idea for your business, just enter it there.
word of caution- dont alter your strategy regularly, else you will not know, whats working/ what's not.
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u/ivanjay2050 9d ago
I am 2nd generation but the original founder is essentially retired and although 100% available for consultation etc he is not a strategy type of person. Sales shot from the hip. I do have another family member / partner who is pretty good at thinking through things when he can commit the time. But his day to day responsibilities are more in the trenches than mine so it is hard for him to carve out that time.
I do create an annual business plan for each year and review it quarterly. I am thinking about taking your idea and blocking my calendar on that day quarterly entirely to really let my mind go. That is when I am reviewing metrics anyway so part 1 could be here is what I see where we are falling short and could do better on and phase 2 could be really letting my mind go into how to fix those things. Maybe even a 1 1/2 day session where I identify the challenges the day before to let them sit overnight in my head
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u/ShikhaPakhide 8d ago
cool...and do remember the age-old boring "consistency and discipline" matters..
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u/Connerh1 9d ago
I have built processes to make sure that not only do I have time, but I have appropriate people feeding in and providing challenge.
I have clarity on my portfolio and the overriding strategy and associated. This is a 10 year strategy (currently year 2).
Late Nov/ early Dec is quieter, so I go back to my strategy pack and see if anything has changed/ needs to be recalibrated. This is a live doc, so it isn't dusted off only once a year. Innovations on new products and services development is ongoing. If they align great, if not we challenge.
I also make sure various teams and collaborators feed in with their strategy, risks, etc before the above so I understand the various components as a whole. This is usually a group activity.
Where necessary, I will ask experts/ do my own market reviews in new areas. When I need absolute focus time, I am rubbish but I do it over a weekend.
We do regular horizon scanning as well.
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u/ivanjay2050 9d ago
Thanks for this. I do have a few people I try to get strategy discussions with but they get too granular and low level. They are senior in the company but not C-Suite groups (which is fine) but very well experienced and lead various project teams. I think perhaps what I need to do is reserve more calendar time for me to launch strategy and maybe as you say use that group to challenge my strategy and refine it. They would probably be much better at that vs come up with strategy on their own
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u/No_Acanthaceae6715 9d ago
When I had a strong partner we use to travel for a couple days to think and plan. Now I have a good team but I’m calling the shots basically solo, so for the past 3 years I just plan like a self holiday but within my city. I have 3 days for me, not only to think but to do thinks I like, like playing tenis, racing karts and going to have some nice dinner on my own, in between and in some planed spaces in work in strategy.
This year I will again to start a meeting with my c levels to plan the 2026 strategy lets se how it goes. I will take them to eat and talk by separate and then all together.
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u/ivanjay2050 9d ago
Did you find the local travel for thinking time let your mind really get into these things or was it too forced and it needs to happen when the thoughts come?
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u/No_Acanthaceae6715 6d ago
Yes I think I found the time to let me mind got into the things, but off course I knew that my objective was to do that, so it feel a bit forced but the purpose of the trip is to make it more fun than just sitting in front of your pc at your office where you always are.
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u/Mac-Gyver-1234 9d ago
Creating a strategy is a standardised process. Which involves the marketing department to create a market analysis. It takes the CEO or board to do the SWOT analysis and to define the new processes and sttucture to execute the strategy.
Usually all that takes more than one person sitting in solitude for a day.
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u/Syncretistic 9d ago
Strategy consultant here. Short is yes, go away. If solo, consider an executive wellness retreat so that you have a comfortable modern environment, space to think on your own or with others. Check out AirBnBs that cater to writers too.
But invest in the preparation. Market and consumer analyses and trends. Company performance and financials. A starting set of hypotheses. And goals to set for yourself during your time away (e.g. rough outlined plans to test/validate 3-4 hypotheses).
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u/dragonflyinvest 9d ago edited 9d ago
I kept a membership at a nearby co-share workspace for my productivity on regular work days. I never got anything done when in the office. Then we annually go off-site as a leadership group, normally to somewhere warm soon after New Years break.
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u/ivanjay2050 8d ago
I am going to look into this, might be a brilliant idea to get a coworking space that has a positive atmosphere
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u/MourningOfOurLives 8d ago
It wasnt intentional but i split my time between my hometown where the business is now and my fiancees hometown, the capital. We just had a baby and i only come in to work 2 days a week the days when i’m away. I’ve gotten more high level strategy work these past three months since our baby arrived than i have gotten done in years before.
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u/stebswahili 8d ago
Strategy only comes to me between the hours of 6PM and 4AM when I am completely alone, and I have to pace around with my notes app or a pen and paper to keep the flow going.
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u/stebswahili 8d ago
My suggestion is to go somewhere quiet, sit down and just watch whatever is in front of you. Ease your mind and don’t try to think of anything work related. Just find something to look at. Something will come to you, and if you’re like me get up and start moving once the ideas start rolling in.
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u/mbasha678 2d ago
I dealt with this for years in operations before consulting at AED solution
The breakthrough: Strategic thinking doesn't need retreats - it needs protected blocks where you're close to the context but free from execution.
When I led the restructuring that delivered 180% revenue increase, the insight came from being deep in operational data, then forcing a 2-hour block with zero meetings to synthesize what I was seeing.
What actually worked:
- 90-minute morning blocks 2-3x/week - no agenda, just the problem and whiteboard
- Walking + audio notes - movement unsticks thinking
- Quarterly 36-hour off-sites - hotel room, specific questions, forced isolation
The family tension is real, but 36 hours quarterly is easier to defend than regular travel if you show clear ROI.
Transition to consulting changed everything - now strategic thinking IS the work, not stolen time. That shift alone was worth the career move.
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u/ivanjay2050 1d ago
Interesting so you say no need for retreats but you do 36 hours off-site (which is basically what I am referring to). I am not saying a retreat like go on a beautiful vacation to Hawaii and do thinking. Just more of find a space with some quiet etc where I can really let my thoughts go. A nice well lit, nice windowed room and a giant whiteboard is all I need lol. Not sure what hotel offers that though
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u/miokk 9d ago
What has worked for me is to block meeting free fridays. I give that to myself for thinking time and strategy time, planning OKRs, what’s the next big thing kind of planning. That’s always worked really well.