The Compass
Embrace Uncertainty. That is Where the Rewards Are!
We are all living in a time of rapid and, in some cases, unprecedented change. The daily economic, political, business, financial, and technological shifts can leave you dazed. Just trying to keep up with all the changes in AI alone is crazy.
In B2B sales, we operate in competitive environments where uncertainty is not just an occasional challenge—it is the constant backdrop against which every deal unfolds. Market conditions shift, buyer priorities evolve, and competition is relentless. Many sales professionals attempt to fight uncertainty by pushing harder, discounting deeper, or relying on sheer effort. But effort alone does not win deals—strategy does.
Strategy is the discipline of creating the power to achieve your objectives in uncertain and dynamic environments.
Discipline is a key word here. The more disciplined you are in developing & executing sales strategies while managing risk, the more freedom you have to maneuver your sales to a successful close. Discipline = Freedom.
The key to thriving in uncertainty is not resisting it but embracing it. Uncertainty is where the perceived risks lie, but it is also where the greatest rewards can be found. Over 75% of the Enterprise deals I’ve closed were not budgeted. We faced the funding uncertainty by creating a compelling value proposition and then working with the Buyer to ‘steal’ the funds from budgeted projects. You know those forecasted deals of yours that slipped with the decision being pushed out? That is because your funding was ‘stolen’ or re-allocated to higher value purchases.
Navigating uncertainty requires more than boldness—it demands a structured approach that enables you to manage risk, adapt your strategy, and position yourself for success. Here are 4 disciplines you can employ as a sales professional or business leader to help you embrace sales uncertainty.
1. Managing Uncertainty Begins with Managing Risk
Acting tactically without a clear strategy is careless. It is the noise before defeat to quote Sun Tzu. Many deals are lost not because of the competition but because of poor risk management. The most dangerous competitor is often the no-decision—buyers who choose to do nothing because they perceive too much risk in moving forward. A competitive sales strategy must include a plan for identifying and mitigating risk, ensuring that uncertainty works in your favor rather than against you.
To manage risk effectively:
· Identify key risk factors early in the deal cycle—budget constraints, internal resistance, competing priorities.
· Develop countermeasures—leverage various deal strategies like Indirect, Divisional or Maneuver to shift buyer perspectives on their perceived risks.
· Maintain flexibility—uncertainty demands the ability to adjust without losing momentum.
A strong strategy does not eliminate risk but provides a framework for navigating it.
2. Detachment: The Key to Observing and Adjusting Strategy
One of the most important skills of a high-performing sales professional—whether a sales leader, salesperson, or business executive—is the ability to step back from the action, objectively see where you are at, adjust your strategy and execute quickly & decisively. John Boyd’s OODA Loop (Observe, Orient, Decide, Act) provides a model for rapidly adjusting to changing conditions. Those who cannot detach from the immediate pressure of the deal will react rather than strategize, making them vulnerable to competitors and Buyers who control the pace of the deal.
Detach in this case means to un-hook, step back or above and look at what is going on objectively. Detachment allows for:
· Clearer assessment of the competitive landscape.
· Better decision-making, free from emotional attachment to a specific course of action.
· The ability to see emerging threats and opportunities before others do.
High performing sales professionals do not just execute—they observe, adapt, and control the flow of the deal. This is also where good sales & business leaders step in. They do deal reviews to contribute unbiased perspective and positive coaching. They help develop the best strategies & tactics to maintain deal momentum and correct course where necessary.
A strong strategy is based on detached, non-emotional, observation.
3. Be Humble: You Never Know Everything
Even the most experienced sales professionals operate with only a fraction of the knowledge required to be an expert in every deal scenario. In uncertain environments, overconfidence can be dangerous. Recognizing the limits of your knowledge allows you to:
· Seek insights from multiple sources (customers, team members, industry experts, AI-powered analysis).
· Stay adaptable rather than rigid in your approach.
· To be curious about the Buyer’s business and seek to understand it.
Uncertainty punishes arrogance but rewards humility. The best strategists approach every deal with a willingness to learn and adjust.
A strong strategy is developed through curiosity.
4. Find Balance: Correct Imbalances in Your Approach
A high-performing sales professional knows how to maintain balance and correct for weaknesses. Just as a fighter must adjust their stance to avoid being knocked off balance, a sales professional must continually adjust to a position of power.
To maintain balance:
· Identify areas of vulnerability—whether it be a weak executive sponsor, lack of internal alignment, or a pricing disadvantage.
· Strengthen weaker areas through strategic plays—Surround Strategy to build internal champions, Divisional Strategy to break down resistance, or Momentum Strategy to attach to stronger initiatives.
· Leverage strengths effectively without overreliance—dominance in one area does not guarantee success in others.
The best sales professionals know that winning deals is about creating power through strategic leverage, ensuring that every move strengthens their position without exposing them to unnecessary risk.
A strong strategy has balance & power.
Conclusion: Make Uncertainty Your Advantage
Uncertainty does not mean chaos; it means you can’t just easily follow the predictable steps of a structured playbook to succeed. You need to navigate by using all the tools at your disposal.
Uncertainty is where the rewards are. Be bold in pursuing deals with uncertain outcomes. Once engaged, stay humble, maintain balance, manage risk and remain emotionally detached to succeed.
Selling into uncertainty is where you make your number!
Navigation:
This Embrace Uncertainty essay is part of the Deal Strategy Series.
Each strategy serves a specific purpose in different competitive deal scenarios.
Next in the Competitive Sales Strategy Series: The Divisional Strategy: When to Use It, When to Avoid It, and How to Execute It for Maximum Impact.
I train sales professionals, business leaders, and their AI agents on Sales and Deal strategies using the Compass AI Sales Strategy system. This training acts as a force multiplier, empowering you and your AI agents to work in alignment to win business and exceed your number in competitive environments.
This was written while listening to ‘Come Join the Murder’ by White Buffalo.
Artwork: Hallway Howell
