Our Services

What We Do

The work we do at Hess Mountain Group sits at the intersection of rigorous thinking and practical action. Whether you need help with funding strategy, organizational risk, or navigating a complex strategic decision, we bring the same discipline to every engagement: honest assessment, clear frameworks, and a commitment to outcomes that actually hold up under pressure.

I structure my practice to preserve time in the field, because that’s where the insights and learning come from. What that means for my clients is focused, high-value engagement as a thinking partner who brings full attention to the work that matters most, on a timeline that works for both of us.

Risk and Decision-making

Many organizations have risk management processes, but few have the cultures and habits needed to change how people think and decide when it matters most.

We help leaders and teams understand why smart people make preventable mistakes: the psychology of rationalization, the gradual normalization of warning signs, and the subtle ways that group dynamics and time pressure distort judgment. We build practical capabilities to counter those tendencies, from checklists and frameworks to more honest conversations about risk tolerance, clearer assessment processes, and debrief practices that create genuine learning.

This work is grounded in graduate-level study, professional consulting experience, and years of high-consequence decision-making in Alaska’s backcountry, where the cost of a misstep can be immediate and unambiguous. The same dynamics that cause teams to rationalize their way into organizational disasters show up with uncomfortable clarity when the terrain is steep and the weather is changing. We bring those lessons back to the table.

Relevant for: leaders navigating high-stakes decisions, teams that have experienced a preventable failure or near-miss, and organizations that want risk management that actually changes behavior.

Strategic Planning

Good strategy starts with an honest assessment of your environment, your capabilities, your assumptions, and the risks inherent in your plans. It also requires the same discipline a good expedition demands, knowing what you’re getting into, planning for what you can’t fully anticipate, and building in the flexibility to adapt when conditions change.

We help organizations develop strategy that is clear-eyed rather than optimistic, actionable rather than aspirational, and flexible for when the plan meets reality. We support environmental scanning, strategy development, plan evaluation, and implementation.

Grant Funding Strategy and Development

For nonprofits, funding strategy is organizational strategy and, like any serious planning effort, the thinking that happens before the execution is where the real value lives.

Developing a grant funding strategy has more in common with expedition planning than most people expect. You’re assessing the landscape, identifying the routes most likely to succeed given your specific capabilities and constraints, making honest judgments about risk and fit, and perhaps most importantly, allocating limited resources toward the opportunities with the highest probability of getting you where you need to go. A scattershot approach of pursuing everything you can find, though far too common, is the equivalent of heading into the backcountry without a map. It wastes energy and produces inconsistent results.

We help organizations develop a coherent, prioritized funding strategy first: identifying the programs that offer the best fit and highest probability of success for your specific situation, building a realistic picture of the effort required, and creating a roadmap you can execute over the next 12 to 18 months. From there, we offer grant writing services to carry the strongest opportunities through to completion. We have particular enthusiasm for working with nonprofits focused on the environment, outdoor recreation and conservation, and animal welfare.

Project Management

Projects often fail in execution, blowing budgets or schedules and failing to meet the initial objectives. Good project management is what bridges the gap between a strong plan and actual results, staying on track through the use of rigorous planning, accountability, and adaptation when conditions change.

We provide project management support ranging from developing plans and accountability structures to serving as an embedded project manager for critical efforts.

Looking for something not listed here? We work across a broad range of strategy and management challenges, and collaborate with other organizations to offer related services. Get in touch and let’s talk about what you need.