Work with Daniel
Master the Art of Agile Strategy
Three Disciplines for leaders who won’t settle for reactive decisions.
How We work
Integrate personal presence with best practices in strategy execution
Two leaders face the same crisis. One reacts from anxiety and creates chaos. The other pauses, sees clearly, and acts decisively, with precision. The difference isn’t intelligence or experience — it’s disciplined practice across three domains, what I call Self-Mastery, Strategic Clarity, and Focused Action. These disciplines integrate personal presence with best practices in strategy execution.
Being a successful leader requires the ability to balance day to day urgency with a big picture vision of where you want to go. Too many well-conceived strategies founder on the shoals of distraction — whether it’s the incessant day to day operational urgencies, or the siren call of bright shiny objects like the latest business best-seller. I’ve worked with a lot of these frameworks, like OKRs, Balanced Scorecard, Management by Objectives and others.
What I’ve learned is that whatever framework you’re using, the biggest factor in success or failure is, quite frankly, your mind. The quality of your attention, your commitment, and your presence are the factors that make a difference.
Agile Strategies offers keynotes, training, workshops and 1:1 coaching to help you and your team develop the disciplines you need to succeed.
Three Disciplines in Practice
Overcome ineffective leadership habits
Agile Strategies offers keynotes, training, workshops and 1:1 coaching to help you and your team develop the disciplines you need to succeed.
“Waste no more time arguing what a good man should be. Be one.” – Marcus Aurelias, Emperor of Rome, 161-180 AD
You cannot lead others effectively if you cannot lead yourself. Self-mastery is the foundation — the capacity to regulate your nervous system under pressure, observe your reactive patterns before they decide for you, and maintain the focus that enables everything else. The practices I teach draw on cognitive science, meditation practice and traditional insights found in time-tested philosophies such as Stoicism.
Outcomes include:
- Nervous system regulation — access to a calm, clear-headed state on demand
- Pattern recognition — seeing the autopilot of your thinking habits before they hijack decision making
- Sustained attention — the trained capacity to stay with what matters, even under pressure
In Practice
When Satya Nadella became Microsoft CEO in 2014, he had a track record as a brilliant technologist. Market cap was stagnant at $300B. The culture was toxic — competitive, political, innovation-killing. He had built his career by being the smartest person in the room, knowing the answers. The traits that had led him to were becoming obstacles. The problems were too big for him to figure out on his own, but nobody felt safe questioning anything he said. One day in a meeting, he realized that his own defensive need to be right mirrored the defensiveness of Microsoft’s culture. He made the decision to move from being a ‘know it all’ to a ‘learn it all.’ He trained himself to pause instead of react, to inquire rather than defend, and to be comfortable not knowing. The culture followed, innovation came back, and today Microsoft’s market cap is 10 times what it was in 2014.
“Do not repeat the tactics which have gained you one victory, but let your methods be regulated by the infinite variety of circumstances.” – Sun Tzu, Military Strategist, 500 BC
Building on the discipline of Self-Mastery, you can develop a greater capacity to zoom out from day-to-day urgency, see all the forces at play. See what others miss, and envision not only what success requires, but what it will take to get there. The practices and philosophies I teach include systems thinking, strategic foresight, and design thinking.
Outcomes include:
- Full-field awareness — seeing market forces, stakeholder dynamics, and timing as one connected system, not isolated events
- Foresight — imagining alternative futures, not just extensions of the past and present
- Creative visioning — imagining what’s needed, grounded in reality rather than wishful thinking
In Practice
After being painfully ousted from Apple in 1985, Steve Jobs spent time in India and studied Zen Buddhism and meditation. This wasn’t a vacation — it fundamentally changed how he thought about innovation and leadership. When he was called back to Apple in 1997, the company had 70 products and 90 days of cash left. Where others saw overwhelming complexity, Jobs simplified the product mix to a 2×2 matrix. This didn’t mean he had a simple view. Far from it. His thinking considered a wide variety of perspectives— those of the customer, competitors, a vision of technology futures, resource constraints and more. But he boiled it down to a simple, easily understood strategy. Four products. The rest is history.
“In preparing for battle I have always found that plans are useless, but planning is indispensable.” –— Dwight D. Eisenhower
Self-Mastery and strategic clarity become real when they show up as influence and execution. This is where your inner work becomes organizational impact. Your grounded presence and stability support both alignment and the flexibility to deal with emerging circumstances. I coach proven strategy execution practices including communications, making and managing commitments, and Objectives and Key Results (OKRs).
Outcomes include:
- Grounded presence — your own state shapes team culture more than your words do
- Service-oriented leadership — creating the conditions for others’ success, with a clear eye on customer value
- Operational discipline — the systems, accountability, and follow-through that turn vision into delivery.
In Practice
Ray Dalio nearly bankrupted his investment firm in 1982 by failing to see the dangers of overconfidence in his economic predictions. This failure forced a painful self-assessment. As a result, he rebuilt Bridgewater based on “radical transparency” embodied in what he called the ‘Principles’ system which included rules for conducting meetings and making decisions, and, most of all, specific practices designed to override his own ego. He began meditating twice a day, a practice he has continued for over 40 years. Today, Bridgewater is the world’s largest hedge fund, and in retirement, Dalio has become a popular and provocative commentator on geopolitics and economics.
Is the Art of Agile Strategy right for you?
This is right for you if:
- You have been successful, but have run into obstacles to moving forward
- You have a natural concern for the people who use your products and services, and for the people who work with you
- You recognize that your state of mind shapes your team’s performance
- You want to respond wisely and compassionately to the stresses of leadership
- You’re open to learning new insights that will make you a better leader
This is not right for you if:
- You’re looking for quick management hacks or silver bullets
- You’re not willing to observe your own patterns honestly
- You believe leadership is about demanding results from others
Meet Daniel Montgomery
Daniel bridges two worlds that rarely meet: business strategy execution and decades of practice in disciplined attention and self-mastery.
He pioneered OKR methodology before it became mainstream, authoring the award-winning Start Less, Finish More, and has spent 40+ years helping organizations — from Fortune 500 companies to mission-driven nonprofits — align vision with execution.
His insight: organizations with brilliant strategies often fail at execution not from lack of tools, but because leaders can’t maintain clarity under pressure.
Daniel holds an MBA, a Master’s degree in Buddhist Psychology, and brings decades of meditation practice across Buddhist, Yoga, and Sufi traditions.
MBA | M.A., Buddhist Psychology | 40+ Years in Strategy Execution | Author, Start Less Finish More
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How We Help
Rather than providing a canned menu of services, I want to get to know you and design a solution that fits your needs. Some of the things I do include: keynote speaking, Training and workshops for executive teams, and 1:1 Coaching
Agile Strategies, based in Boulder, Colorado, helps leaders develop the inner capacities and practical tools for self-mastery, strategic clarity, and focused action. Drawing on decades of experience with OKRs, strategic foresight and planning, and disciplined practice, we help leaders stay grounded, see clearly, and act with intention in complex environments.
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