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Thought Leadership

Entry Points and Long Games: How Small Engagements Build Big Relationships

Thought Leadership

Entry Points and Long Games:

How Small Engagements Build Big Relationships

By Alicia Darrow and Cass Moore

The fastest path to a major client relationship is often through a small, well-executed piece of work. 

Not because small work leads to big work automatically, but because it gives the client an early experience of how you operate. How you think. How you handle problems. Whether delivery matches what was promised. That experience builds trust, and trust is what generates the next conversation. 

 

What’s an entry-point engagement? 

It’s a small, well-defined engagement that creates access without the overhead of something larger. 

It might look like a discovery sprint, strategy session, proposal or website audit, or short-term pilot. A clear deliverable and defined end date. This is designed to demonstrate how the work is done, not just what is produced. 

The distinction matters. Most small engagements are treated as contained transactions, efficiently delivered, then closed out. The ones that lead to long-term relationships are approached differently as the beginning of a much longer relationship. 

 

How to approach them differently 

Be more curious than the scope requires. Ask what this work connects to. What would the client need to be true six months from now for it to have been worth doing? That level of thinking distinguishes a strategic partner from a vendor. 

Deliver exactly what was committed—on time, with clear communication. Scope creep is a fast way to erode a new relationship. Consistency builds more trust than unexpected extras. Leave something behind that makes the next conversation natural. Something that carries the conversation forward. A set of questions or relevant observation. Context that connects to what comes next; not a pitch but something that keeps the relationship active beyond the deliverable. 

 

The longer game 

Getting in the door is a strategy. What happens next determines whether the relationship continues. 

We have seen this pattern consistently. A firm wins a modest engagement and uses it as an opportunity to demonstrate how they work, not just what they produce. The client experiences the work directly and trust builds. When the larger opportunity surfaces, there is little competition because the relationship is already doing the work. 

The opposite happens just as often. The work is delivered, then closed. No follow through or ongoing connection. The client moves on because there was nothing to anchor the relationship beyond the deliverable. 

An entry-point engagement is not just a project; it is the start of a strategy. The question moves beyond what’s to be delivered, to a greater understanding of what this engagement needs. This demonstrates to the client the intention to continue the relationship. Start there. 

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Thought Leadership

Capture, Positioning, Pre-Pursuit: Different Words, Same Competitive Advantage

Thought Leadership

Capture, Positioning, Pre-Pursuit:

Different Words, Same Competitive Advantage 

By Alicia Darrow and Cass Moore

Capture is one of the most misunderstood words in business development. We were on a call recently with someone smart, experienced, and deeply familiar with BD. When the word came up, her first question was: is that just a new name for sales manager? 

It was a fair question. And it is exactly the problem. 

Capture as a concept is not new, and it is not just a title. It is the practice of strategic positioning before an opportunity is formally open. The relationship-building, market intelligence, internal alignment, and win theme development; everything that happens before the RFP drops. In the architecture, engineering, and construction world, it has a name. In most other industries, the same work exists under different language: pre-positioning, pipeline development, account strategy. While the terminology varies, the discipline is the same. And in every industry, it is the difference between responding to opportunities and creating the conditions to win them. 

 

When every opportunity feels like an emergency 

The RFP arrives and all hands are on deck. The proposal gets written within a tight turnaround time. The client relationship is thin, the timeline is brutal, and the opportunity showed up unannounced because nobody was tracking it. That is not a pursuit. It is a response. 

The team cannot clearly articulate why they are chasing this one beyond the fact that the work looked relevant. 

It’s exhausting and expensive. A path to team burnout. Every proposal submitted without a realistic path to winning costs real time, energy and resources. And the organizations that stay stuck in reactive mode tend to keep submitting the same way, losing at the same rate, and absorbing it as a cost of doing business. At some point that stops being a pipeline problem and starts being a strategic one. 

 

Positioning is different. It starts with a relationship, a problem worth solving, and enough lead time to do something with that knowledge. By the time the RFP hits, the team is not scrambling. Rather, they have already identified the right subject matter experts and have already had the conversation about win themes. The work for the proposal is well underway; project descriptions and resumes are customized for the work. The team is not flailing about trying to figure out who belongs in the room, because that conversation happened months ago. 

 

The Strategy Department’s definition 

Strategic positioning for winning opportunities. Not just for RFP-driven work, but for any kind of program, contract, or client relationship worth pursuing intentionally. It includes attending the right conferences and performing market research on a prospect before reaching out. Making a warm connection through a shared network, and showing up with something useful before there is anything to sell. 

This is capture regardless of what vernacular is used. And it applies far beyond firms that respond to formal tenders. Founders, consultants, professional services firms, anyone who wins workthrough relationships rather than transactions is doing some version of this, whether they have named it or not. 

 

The earliest signal that an organization is ready to build this practice 

They understand the work they do before an opportunity opens determines the outcome. That conviction, starting with leadership, is the foundation. Without it, capture stays a concept. With it, the vocabulary and the process follow. 

The organizations that have made this shift most successfully did not just name the practice. They built the infrastructure: shared language, structured pipeline conversations, consistent intelligence gathering, and the discipline to say no to pursuits where they are not positioned to win. 

That last part is the hardest, and it is where the real advantage lives. 

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Thought Leadership

Are You Working for Your Social Channels, or Are They Working for You?

Thought Leadership

Are You Working for Your Social Channels,

or Are They Working for You?
By Alicia Darrow and Cass Moore

It’s easy to get excited about using the many social media platforms available to grow a business. Someone might say what has been working for them, and it gets added to the stack. In a recent conversation with a founder, we learned she was using a total of four platforms: Facebook, LinkedIn, Instagram, TikTok. Then she described what it takes to manage them. Posting, responding, organizing a group, monitoring channel engagement, every week. 

When asked which ones were moving the business forward, she paused. That pause is where the real conversation starts. 

To us, it sounded like managing a schedule instead of implementing a strategy.  

The more-is-better approach to social media is one of the most common mistakes we see. Businesses spread themselves thin across too many platforms and maintain each one out of obligation, and then wonder why the effort is not converting to desired results. Most of that effort is feeding the channels, not the business. 

 

The question that brings clarity 

Before any conversation about which platforms to use, there is a more important question: where are the people you want to reach? 

Most channel decisions get made based on what feels active or what peers are doing. Market research answers this more reliably than intuition does. Where are your ideal clients spending time online? What are they reading, sharing, responding to? What does your existing client base look like, and where did those relationships start? Those questions have answers, and the answers drive the decision. 

Show up where your ideal clients already are. If they are senior decision-makers, they are on LinkedIn. They are not scrolling Instagram at noon looking for your content. The wrong room, no matter how often you show up, is still the wrong room. 

 

Busy is easy to mistake as progress. 

Responding to comments on a platforms that have never generated a single inquiry. Repurposing the same content everywhere and calling it a strategy. Tracking engagements while questioningwhy revenue is not moving. That is activity, not strategy. 

We had a conversation with a founder who wanted higher-value clients, corporate contracts, and programs that generate more revenue. We asked her: of the four platforms, which one is the most likely path to those outcomes? She knew the answer. It was not all of them. 

That is not a reason to abandon every channel, but it is a reason to be honest about which ones are driving results and focus there. 

 

On the ROI and trust-building stage 

Social presence is slow. Organic reach does not convert on a predictable timeline. Some audiences move quickly; others take time. That variation is normal and reflects factors nobody fully controls, including algorithms, audience behavior, and content reach. 

What can be owned and measured is consistency, clarity, and relevance. Those are the inputs. Impressions, engagement patterns, and audience growth are the leading indicators. Revenue conversion follows, with a clear and intentional infrastructure in place. While likes do not pay the bills, the answer is not to push harder on the wrong platforms. It is to build the right channel foundations that are working for you and stay consistent long enough for it to matter. 

 

What to ask before you hire a social media manager 

Before brining someone in to manage your social presence, start with one question: what should this channel produce, and for whom? 

Not which platforms you want to be on. What outcome matters, and where the right audience is already paying attention. Strategy and execution are both necessary. The mistake is starting with execution before the strategy exists. 

Otherwise, you are handing someone a schedule and hoping it turns into something. 

We work with organizations on both sides of this: building the strategy that determines where to show up, and managing the execution once it’s clear. If either piece is missing for you right now, let’s talk. 

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Thought Leadership

New Year’s Resolutions: You Don’t Need More Discipline. You Need a Different Strategy.

Thought Leadership

New Year’s Resolutions:

You Don’t Need More Discipline, You Need a Different Strategy
By Alicia Darrow and Cass Moore

Let’s make a guess: You made it three weeks. 

Maybe four if you were really committed. The morning routine. The commitment to health, or the networking plan. Maybe your revenue goal has been broken down into monthly milestones. 

And now? It’s the middle of February and you’re already negotiating with yourself about why next month will be different. But it’s unlikely to change; New Year’s resolutions don’tfail for lack of discipline, they fail because they’re disconnected from who you actually are. 

We’ve repeatedly watched leaders set ambitious Q1 targets, only to abandon them by Valentine’s Day. It’s easy for growing businesses to create elaborate strategic plans that collect dust by March. The pattern is usually the same: external pressure, rigid structure, inevitable failure, quiet shame. Ugh!  

At The Strategy Department™, we don’t do resolutions. We choose words. 

Cass chose GENEROSITY. Alicia chose EMPOWER. 

A word of the year works differently than a resolution. It differs from a checklist or milestone. It’s a compass that serves as your true north when decisions get complex and the path forward isn’t clear. 

Take a real scenario: A potential client wants to move fast, but the timeline feels impossible. The resolution might say “increase revenue by 20%”, which pushes you to say yes regardless of fit. But Cass’s word, GENEROSITY, asks a different question: Does this partnership create space for real impact, or does it extract value for short-term gain? 

Through that lens, the outcome might be the same, but the difference, the nuance, is in the framework.   

The power is in the layers. Generosity doesn’t just mean one thing for Cass. It shapes how she partners with clients, how she invests her time, how she measures success. It’sabundance over scarcity. Impact over accumulation. Long-term relationships over short-term wins. 

When a colleague asks for her expertise, generosity guides the response. When she’s considering a new service offering, generosity filters the decision. When she’s allocating her calendar, generosity determines what gets priority. 

Empower works the same way for Alicia. It started as a challenge to herself: stop waiting for permission, trust her decisions, move with confidence. And it ripples outward. 

When she’s in a client meeting and sees an opportunity to redirect their approach, empower pushes her to speak up instead of staying silent. When she’s stuck in mental gymnastics about whether to run something by Cass first, empower cuts through: trust your expertise and move. 

When a team member hesitates on a decision, empower reminds her to model the confidence she wants to see. 

Words stick because they evolve with you. Alicia wears a bracelet with EMPOWER. It’s a talisman, a physical reminder when the mental gymnastics start creeping in. 

In a tense negotiation, she sees her word: Empower. The decision becomes clearer and easier 

During a morning when the inner critic is deafening, she sees it on her wrist: Empower. The narrative shifts, anxiety dissipates and groundedness is present. 

That bracelet sparks conversations with friends, check-ins with Cass, moments of recalibration when she’s second-guessing a decision. While on the outside it may appear to beaspirational, at the root, it really is operational. 

It’s about presence over perfection.  

Your word becomes your personal brand in action. It’s the golden thread that connects how you lead, how you communicate, how you make decisions. It’s not what you do, but it’s who you are when you do it. When examined, you may recognize that it’s something that likely ties directly into your team or personal values.  

Here’s the truth about resolutions: They fail because they’re external targets imposed on yourself, often rooted in “should” instead of “am.” They’re built on discipline, willpower, and shame when you fall short. 

Your word of the year (or even years)? That’s different. It’s rooted in your values, your strengths, and your story. It doesn’t demand you become someone else. It asks you to become more yourself. 

When Cass chooses generosity over scarcity in a difficult conversation, she’s not following a resolution. She’s being herself, more intentionally. 

When Alicia trusts a decision without seeking permission, she’s not checking off a goal. She’s embodying her word. 

As we move deeper into 2026, the question isn’t whether your resolutions are still intact. 

The question is: What’s your word? And how is it shaping the decisions you’re making today? 

Want to discover your golden thread?

We’ve created a Personal Brand Discovery guide to help you uncover the themes, values, and strengths that define who you are—beyond your job title. Download it here and find the word that will guide your year. 

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Thought Leadership

Not Every Plan Lands—But Every One Teaches

Thought Leadership

Not Every Plan Lands—But Every One Teaches
What failed? Not the vision but the scaffolding around it.
By Alicia Darrow and Cass Moore

Even the best-designed strategy sessions can falter without the right structure, leadership alignment, and organizational readiness—especially when scope shifts, timelines stretch, and virtual formats expose underlying fractures. This is a story of how one engagement unraveled, what we learned from it, and why honest reflection is just as valuable as a polished outcome.


We had a clear path: a focused, in-person strategy session with ten-12 key decision-makers. Then everything shifted.

What started as a tightly scoped engagement became something much broader. More voices entered the room: some essential, some emergent. The format changed, driven in part by what felt like a lack of support from leadership, even though this was a priority initiative in a growing market. The session moved from in-person to entirely virtual. And the timeline stretched from a few concentrated days to a drawn-out, months-long effort.

What initially felt efficient—early alignment and clear workstream identification—began to drain morale and resources. What happened then was momentum faded and expectations blurred.

This isn’t unusual. But it is a cautionary tale, which we’re viewing as a growth opportunity.


3 Lessons from the Pivot

1. Strategy Needs a Container—Especially When Everything Else Changes

Great strategy requires structure, not just vision. When the original frame (people, time, place) changes, the work must be restructured to maintain clarity and momentum. We learned that without a strong container, even good ideas can drift.

2. Expanding Voices Expanded Complexity

Bringing more stakeholders into the conversation surfaced valuable insights—but also introduced friction, and at times, confusion. We shifted from facilitation to orchestration, trying to maintain engagement while holding the thread of a cohesive direction.

What did that actually look like?

Breakout rooms with facilitators and note-takers. Multiple perspectives needing synthesis after each session. More logistics, more follow-up, and more risk of losing nuance in translation. The demands on time and resources grew without a guarantee of forward movement.

Still, there were bright spots. We used the shift as an opportunity to bring in guest subject matter experts who added depth and challenged assumptions. Their input revealed new angles in our target market and helped us clarify whose voices truly needed to be in the room moving forward.

More isn’t always better. But sometimes, it’s necessary to go wide before you can go deep.

3. Virtual Strategy Requires More than a Platform

Teams (or Zoom) isn’t the enemy and it’s no substitute for the trust that’s built in the room. To adapt, we shifted to sprints—or what we called “bursts”—designed with space for digestion, reflection, and realignment between sessions. Coaching helped keep decision-makers tethered to the bigger picture. In theory, the extended timeline could have strengthened long-term buy-in.

However in practice, we found there were too many side conversations outside of those bursts to check in on low engagement from key participants. We had to ask the hard questions: Is this person truly vested in this strategy? Are they even interested in growing this market? So many layers that required excavating.

Those questions eventually sparked deeper leadership conversations. They also highlighted a structural challenge: too many people involved in shaping strategy without clear roles or ownership. What could have been energizing instead became “just one more hat” to wear.

In systems where consensus is prioritized over clarity, and decision-making is diluted across too many voices, momentum stalls—and everyone feels it.


Strategy in Motion

Virtual strategy sessions can be highly effective and increasingly, they’re the norm. With the right design, facilitation, and commitment, remote work doesn’t have to mean diminished results.

Unfortunately this particular engagement was set up for struggle from the start.

The format shift wasn’t the issue—it was everything surrounding it. Leadership transitions, unclear ownership, wavering priorities, and a lack of internal alignment made it difficult to maintain momentum. The result was a drawn-out process that lost energy over time and left some participants, and even some leaders, disengaged.

Still, we don’t view it as a failure. We view it as a case study in what happens when strategy work lacks the structure—and sponsorship—it needs to thrive and succeed.

We walked away with clear takeaways:

  • Strategy needs a strong container, regardless of format.
  • Leadership alignment is imperative (otherwise strategy doesn’t stand a chance).
  • Process design must reflect the reality of the organization’s capacity, not just its ambition.

Not every engagement sticks the landing. But each one teaches us something. And we bring those lessons into the next room—virtual or otherwise.

Your Turn

Finding your strategy process slipping off course? You’re not alone. Let’s talk about what’s still possible—and how to move forward, even when the original plan no longer fits.

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Thought Leadership

From Siloed to Strategic: Lessons from a Business Transformation Workshop

Thought Leadership

From Siloed to Strategic: Lessons from a Business Transformation Workshop

By Alicia Darrow & Cass Moore

True business transformation starts when teams stop just planning and start confronting the real barriers. It’s in those honest conversations and bold visions that real change takes root.

“If we don’t feel uncomfortable, we probably haven’t done our job.”

One of the participants said this during an Operational Health and Safety strategy workshop, and it’s been stuck in my head ever since.

This wasn’t your typical planning session with flip charts and sticky notes. We were there to shake things up—to challenge the way this team had always done business and help them see what was actually possible.

The Reality Check: Great Work, But…

Here’s the thing about this team: they were really good at what they did. The technical work was solid, clients were happy, and projects kept coming in. But scratch beneath the surface, and you’d see the cracks.

Everyone was working in their own little bubble. The West Coast team rarely talked to the East Coast team. The technical folks stayed in their lane, and the business development people stayed in theirs. Sure, they were busy, but they were stuck in a cycle of small, one-off projects instead of building the kind of deep client relationships that really move the needle.

When they talked about doubling their market in five years, it felt less like a vision and more like wishful thinking. Something had to change—not just in how they worked, but in how they thought about their work.

The Workshop: Getting Uncomfortable (On Purpose)

We knew we couldn’t just throw another strategic planning template at this team. They needed something different: part provocation, part collaboration.

Before we even got in the room, we had them do some homework: SWOT analyses, stakeholder surveys, vision-setting by region. Then, during the actual workshop, we mixed things up with real client stories, live testimonials, and hands-on exercises that forced them to look at their business through fresh eyes.

Some of my favorite moments:

  • Client stories that opened eyes: Nothing beats hearing directly from clients about what they actually value (spoiler alert: it wasn’t always what the team thought)
  • Visual mapping: We used MURAL to help them literally see the growth opportunities they’d been missing
  • “Start/Stop/Keep” sessions: Making strategy concrete by asking, “What do we actually need to change?”
  • Giving the younger folks a voice: The young professionals became our secret weapon—they asked questions the senior team had stopped asking years ago

We pushed them to dream bigger while also getting practical about what it would really take to get there.

What We Discovered (And What Surprised Us)

As the conversations got deeper, some really interesting patterns emerged:

The growth mindset shift was real. Once people started talking openly about being stuck in a “same old, same old” mentality, they couldn’t unsee it. Suddenly, everyone was asking why they’d been playing it so safe.

Collaboration wasn’t just nice-to-have—it was essential. The “aha” moment came when they realized their biggest opportunities required expertise from multiple regions and functions. No more going it alone.

Quality over quantity. Instead of chasing every RFP that crossed their desk, they started talking about choosing clients more strategically and building real partnerships instead of just completing projects.

The next generation was ready to step up. Some of the best ideas came from the younger team members, and the senior leaders started to see them as future business builders, not just technical contributors.

Leadership had to show up differently. The days of “set it and forget it” planning were over. Real growth meant getting hands-on, removing obstacles, and actually following through.

Naming the elephants in the room. From talent shortages to “that’s not how we do things here” thinking, they finally started talking about the real barriers holding them back.

What Changed (Beyond the Buzzwords)

By the time we wrapped up, this team had:

  • A growth vision that actually excited people
  • A clear picture of where they needed stronger leadership
  • A prioritized list of clients worth investing in
  • Concrete plans for working across regions
  • New ways to stay connected and track progress

But here’s what mattered most: they were talking to each other differently. There was an energy in the room that hadn’t been there before—a sense of “we can actually do this” instead of “maybe someday.”

The Real Lesson

We know one workshop isn’t going to solve everything, but it can be the spark that gets things moving.

When you give people permission to be honest about what’s not working, challenge them to think beyond their current reality, and support them in figuring out how to get there, something shifts. The conversation changes and the possibilities expand.

Real strategy really is about changing how people see what’s possible and getting them excited about building it together.

Sometimes transformation doesn’t require a complete overhaul. Sometimes it just requires getting in a room, asking better questions, and being willing to get a little uncomfortable in the process.

What’s keeping your team playing it safe? We’d love to hear about the workshops or conversations that actually moved the needle for you.

Strategy that grounds you. Growth that moves you.™