Summer is often underestimated in the world of growth-stage startups and early-stage investment. While many founders and investors see these months as a time when sales slow down and decision-makers take vacations, the most successful leaders know that summer is a strategic window. It is a season when competitors relax and founder opportunities to deepen relationships, gather market intelligence, and accelerate growth are ripe for the taking.
If you are a founder at the Seed or Series A stage or an investor seeking signals of operational excellence and customer-centric thinking, this is your moment to stand out. The key? Re-engage past clients with intention and purpose. Below, we explore why this strategy works, the exact questions to ask, and how to turn these conversations into a competitive advantage for the rest of the year.
Why Past Clients Are Your Secret Summer Advantage
According to research by Harvard Business Review the cost of acquiring a new customer is five to 25 times higher than retaining or reactivating an existing one. Past clients already know your value, have experienced your product or service, and are more likely to respond honestly to outreach. Yet, in the rush to win new business most founders neglect this valuable network, especially during the summer lull.
For investors, founders who proactively engage past clients demonstrate a sophisticated understanding of customer lifetime value (CLV), retention, and market fit. These are the very metrics that drive sustainable growth and signal readiness for future funding rounds. Summer is also a unique time. Decision-makers are less inundated with cold outreach, making your message more likely to stand out. Moreover, with annual planning and budgeting on the horizon, your insights could influence their upcoming decisions.
The Five Questions That Unlock Growth
To maximize your summer outreach avoid generic check-ins or sales pitches. Instead, use these five questions that have been influenced by my 26 years’ experience, and from insights in Forbes, McKinsey, and Harvard Business Review to spark meaningful conversations and unlock actionable growth opportunities for you.
1. What Did You Value Most About Working With Us?
This question does more than stroke your ego. It reveals your true differentiators in the eyes of the market. Clients might highlight aspects of your service, responsiveness, or product features that you take for granted. Their answers can shape your marketing, inform your product roadmap, and even provide compelling proof points for investor updates and pitches.
2. Where Did We Fall Short or Leave Room for Improvement?
Honest feedback is a founder’s best friend. By inviting constructive criticism, you uncover blind spots and process gaps that may be holding you back from repeat business or referrals. According to HBR.org, companies that systematically act on customer feedback see higher retention rates and faster revenue growth.
3. What New Challenges Are You Facing This Year?
Markets evolve quickly, and your clients’ priorities may have shifted since you last worked together. By understanding their current pain points, you can tailor your offerings, propose new solutions, or even co-create products that address emerging needs. This question also positions you as a long-term partner, not just a vendor.
4. Would You Recommend Us to Others? Why or Why Not?
This is a direct route to referrals and testimonials. It also surfaces any lingering concerns that you can address to turn detractors into promoters. According to Harvard Business Review, companies that actively solicit and act on referral feedback grow faster and more efficiently than those who do not.
5. Is There Anything You Wish We Offered or Did Differently?
Clients often have creative ideas for new features, services, or delivery models. Their suggestions can inspire your offering’s next iteration, unlock new revenue streams, or help you identify gaps in the market before your competitors do.
How to Make the Most of Every Conversation
The value of these questions is magnified by the way you approach the conversation. Here are best practices drawn from leading business thinkers:
- Personalize your outreach: Reference your previous engagement, specific results, or unique aspects of their business. This shows that you value the relationship versus just sending a mass email.
- Listen more than you speak: Let clients share openly. Take notes, ask follow-up questions, and resist the urge to pitch unless invited.
- Act on feedback: Implement changes where possible and follow up to let clients know how their input made a difference. This closes the feedback loop and builds lasting loyalty.
- Document and analyze: Aggregate the insights you gather to identify patterns, inform your strategy, and share learnings with your team and investors.
Why Investors Are Watching This Metric
For Seed and Series A investors, customer engagement and retention are critical signals of product-market fit and founder discipline. Founders who actively engage past clients demonstrate a growth mindset, operational rigor, and a willingness to learn those qualities that de-risk investment and increase the likelihood of outsized returns. Moreover, the insights gathered from these conversations can fuel investor updates, board meetings, and fundraising decks. Real-world testimonials, clear evidence of repeat business, and a pipeline of referral opportunities are powerful proof points in a competitive funding environment.
Too many founders let the summer slip by, waiting for the market to pick up in the fall. The reality is the groundwork for Q3 and Q4 success is laid now. By reaching out to your past clients with these five questions, you can spark new opportunities, generate referrals, and gather the insights you need to refine your strategy for the rest of the year.
If you are ready to turn client conversations into real revenue growth, GrowExpand.com’s Rapid Revenue Roadmap is purpose-built for founders and investors who want actionable strategies and measurable results. Our process helps you reconnect with your best clients, uncover new opportunities, and accelerate your path to growth. Schedule your Rapid Revenue Roadmap session today and set the pace for the rest of the year. Do not let your competitors catch you napping—your next breakthrough could be just one conversation away.
Unlock growth where others see a slowdown. This summer, make every client conversation count.
This post was written by Rich Laster
The views and opinions expressed on this blogpost are solely those of the author, and do not represent the views of GrowExpand.com, our staff, our partners, or our clients. The material and information contained on this blog is for general information purposes only. You should not rely on said information in making legal, accounting, or other business decisions in the absence of expert counsel.
Sources: Harvard Business Review, McKinsey, Forbes, Crunchbase