Breaking Down the Last 10 Deals: Learning from Wins & Losses

Borrowed

"Many times in business we get a big win and then we coast. Instead of continuing to play to win, we are now simply playing not to lose. We get cautious and lose our energy and our drive. Creativity and innovation soon disappear. And by trying not to lose, we find we are losing even more. We lose our fire. We’ve lost the innovative spirit. We begin to doubt ourselves."

From "Straight-Line Leadership" by Dusan Djukich [Book]

Learned

Q4 has brought some good momentum for new business. While a lot has changed over the past several months and there's no single factor to attribute, our recent CPG-focused positioning and services evolution has sharpened how we qualify leads—both in the calls we take and the proposals we send. If not within our ideal client profile (ICP)—which, for these purposes, we'll define as CPG— we want to be sure the client's needs align with our strengths and vision as an agency.

The quarter isn't over yet, but here’s where we stand:

• Calls taken: 34% of leads
• Proposals sent: 60% of those calls
• Wins: 67% of closed opportunities (with some still pending)

Compare that to Q1-Q3, we averaged:

• Calls taken: 53% of leads
• Proposals sent: 50% of those calls
• Wins: 28% of closed opportunities

It's worth noting these numbers are inbound leads only and don’t account for deals spanning quarters.

In a nutshell, we took more calls, but sent less proposals and won at a lower rate. Looking at this comparison, I’m reminded of the pressure of long, slow sales cycles and how it pushed us to pursue opportunities without the same clarity or rigor we have now. It’s a good reminder of why investing in generating more qualified opportunities matters—so we’re never in a position where we’re chasing whatever comes through.

Next year, we’ll be experimenting with outbound again, this time with lessons learned from our 2023 efforts.

Themes & Lessons

With the recent momentum, it’s easy to ride the wins and brush off the losses, but I see value in reflecting on both. So, I thought it would be worthwhile to review the last 10 deals where we sent formal proposals to see what contributed to the outcome. This does not include open opportunities or calls that didn't lead to a proposal.

Half of all these leads were CPG. Of the six losses, three were not but we felt confident in our ability to add value and/or they came through warm referrals.

Here are five recurring themes and takeaways; nothing necessarily new, but all helpful lessons within the context.

1. Engage decision-makers early: Surprises from stakeholders joining late can derail deals.
2. Flexibility builds trust. Providing multiple approaches or pricing options creates room for collaboration with the client.
3. Educate where needed: First-time agency clients, or those burned by agencies in the past, especially benefit from clear guidance on process and collaboration.
4. Never assume a win: Verbal commitments aren’t contracts—stay sharp, paying close attention to priorities and concerns, until the deal is signed.
5. Patience pays off: With strong communication and patience, longer sales cycles reward trust-building and persistence.

Last 10 Deals Breakdown

Okay, let's dig into the deals, starting with the most recent. For each, I'll share the lead channel, outcome, and relevant details.

1. Referral – LOST

• Pricing exceeded their budget, and their marketing agency recommended another partner, citing “efficiencies of the teams working together.”
• Takeaway: While we provided multiple options with ranges in pricing and projected ROI, a new stakeholder on the last call shared some unexpected priorities. I'm not sure I'd change much about our proposal given the information we had; however, getting access to all decision-makers upfront could have helped. This experience also reinforced the importance of building strong agency partnerships.

2. Referral – WON

• This was the 18-month sales cycle I recently wrote about. The client came through a warm referral and appreciated the research and audits we delivered during the process.
• Takeaway: This was a win due to consistent trust-building and delivering value throughout the sales process. Patience and persistence paid off.

3. Referral – LOST

• With a new stakeholder joining and the IT Director stepping away, we weren’t sure this project would ever take off. In the end, the client felt another agency’s approach was “more comprehensive.
• Takeaway: Given the project requirements, we recommended a discovery phase to finalize our approach but didn’t offer alternative options. Investing in research to present a robust all-in solution upfront might have made the difference.

4. Referral (CPG) – LOST

• This client had only worked with freelancers in the past but was looking to invest in an agency. They chose another agency that shared more insight into their process and offered bundled pricing for the project and ongoing maintenance.
• Takeaway: First-time agency clients need extra education on process and collaboration. I stand behind our proposal options, but we might have won with more attention to their creative needs and an all-inclusive proposal, something to consider for clients like this where e-commerce is not the main channel.

5. Google Search (CPG) – LOST

• The project was taken in-house for cost reasons. They had a formal RFP and before our first call, we pre-qualified the opportunity via email, including the budget range. Founders joined the proposal call, seemingly out of the loop, and questioned the investment (another retail-focused CPG brand).
• Takeaway: While the timeline for a proposal was tight, pushing to meet with the founders before presenting a proposal might have led to us passing on this or taking a different approach.

6. Google Search (CPG) – WON

• The COO found us through Google and recommended us to the CEO, who felt confident after our initial conversation and later, through my LinkedIn content.
• Takeaway: The interesting thing about this one is I sent an informal proposal via email with no response. Weeks later, they wrote back eager to move forward. A few takeaways here: lead with curiosity on the first call, be persistent and communicative, and focus on the value of the proposal first—format second. It's also cool to see how content can build trust, even if engagement metrics don’t show it.

7. Partner Directory – WON

• I remember leaving our first call with this client with a gut feeling it would be a win. But it took time. They had put in a lot of upfront work outlining their needs, and in the end, they valued that we took the time to understand and craft an approach that aligned with them.
• Takeaway: Even when it feels like a sure win, patience is critical. Staying flexible helped us navigate unexpected delays and arrive at a solution together.

8. LinkedIn Lead (CPG) – LOST

• Budget constraints.
• Takeaway: The client was vague about their budget, but we pursued the lead because it was CPG. Luckily, we didn't spend too much time on a proposal but in hindsight, this probably wasn't a good fit.

9. Referral (CPG) – WON

• Trust-building was key. The client had negative past experiences with agencies and platforms, so we focused on education and multiple approach options.
• Takeaway: The client didn’t choose any of the three proposal options we presented. Instead, their feedback shaped our final engagement—a great example of how presenting options can spark dialogue, even when the project and budget seem clear.

10. Referral – LOST

• The client initially expressed a desire to move forward but ultimately, chose another agency they felt had stronger expertise in a key area.
• Takeaway:  Never assume the win is in the bag! This was a bummer because I know we could have delivered on what they needed. But we missed how important it was to them and didn’t demonstrate our expertise.

Wins give us energy; losses give us insight. Both have left us with lessons we’ll take into 2025 as we refine how we qualify, engage, and deliver value to clients.

Thought

What was a low point this past month, and what did it teach me? A high point?