How to Retain and Upsell Your First Few Clients?

Most new entrepreneurs struggle to grow their business because they focus more on the acquisition, and less on retention or upselling their initial clients…

But why does this happen?

Well, mostly because these entrepreneurs underestimate the value of their current deep relationships. The ‘high’ they get from acquiring a new client is stronger, that’s why they divert their attention elsewhere. 

And because of this, first clients can feel undervalued and start looking elsewhere for solutions, leading to a high churn rate and missed revenue opportunities.

…Hence why mastering client retention and upselling is crucial!

In this article, I’ll walk you through:

• Understanding Your Client's Long-term Needs and Goals

• How To Drive Continuous Value

• Working To Build a Consistent, Strong Relationship

• Timing Your Upsell Accordingly

Let’s dive in. 🚀

Understanding Your Client's Needs and Goals

Every successful retention or upsell begins with a deep understanding of your client's unique needs and goals.

I want you to have less of a service approach and more of a business approach.

What I mean by that is pay less attention to what services you want to sell, and more on how to grow your clients’ business through that service - you’ll become more valuable that way.

Think about it!

If you have someone who’s working as an additional brain to grow your business, you’d be more likely to trust (and keep) them. It’ll be like having another business partner. So when you tailor your approach based on a deep understanding of your client, you not only satisfy their current business needs but also pave the way for natural upsell opportunities. 

However, a common mistake is to assume all clients have the same goals, which can lead to irrelevant offers and dissatisfaction.

To avoid this, make it a practice to conduct thorough onboarding interviews, aiming to uncover not just the surface-level needs but the deeper business goals behind them.

For instance, if you're dealing with a client who needs digital marketing services, go beyond just understanding their target metrics. Learn about their ideal customer profiles, sales funnel stages, and what success looks like to them. This will help you with the insights needed to offer truly valuable upsells in the future.

This is how you set the stage for a fruitful, long-term partnership.

Demonstrating Continuous Value

If you want your client to pay you regularly, you need to drive continuous value to the client's business.

Regularly reminding your clients of your contributions is crucial for retaining them and setting the stage for successful upsells. A great way to practice this is to stack your skills based on complementing fields. If you learn social media marketing, try upskilling yourself in project management too, and slowly take over that area to free up your client’s time. 

The more areas of your client’s business you handle, the more valuable you become to them.

However, many businesses make the mistake of not communicating their achievements and ongoing efforts effectively, leading to their value being overlooked.

For this, implement a robust system of monthly reporting that not only highlights what has been achieved but also what is being worked on and future suggestions for improvement. 

If you’ve enhanced a client's website speed significantly, don't just stop at delivering the improved metrics. Show them how this improvement has reduced bounce rates, and how it's expected to enhance user engagement, and discuss potential next steps to capitalize on this progress, such as improving the mobile user experience or A/B testing landing pages.

This won’t only reinforce your value but also seamlessly introduce more opportunities for the future as things progress!

Let's now turn our attention to building a strong relationship with your clients.

Building a Strong Relationship

This may seem straightforward, but it’s more deeper than it looks.

The trust factor is key to loyalty, making clients more open to considering your upsell offers. 

I don’t want to discourage you, but I’ll be direct here…

I want you to understand (and acknowledge) that MILLIONS of people can provide the same service you do. Maybe the same, maybe better, maybe for cheap.

That’s what the world is like now – globalization comes at a cost!

But that said, ask one question to yourself:

“How can I differentiate myself from my competitors?”

And to answer this, I recommend 2 approaches:

1. Understanding your client’s needs and delivering continuous value (basically everything we already discussed) 

2. Build a genuine, humane relationship with them.

I remember when I visited Pakistan recently to meet my family, and by chance, my team members from Investing at 25 were in the same city!

So after 1.5 years of working fully remotely, we three finally met up and had lunch together.

Though they are not my clients, it’s the other way around - but I’m more likely to trust them to deliver on a new task than to hire a separate person to fulfill it. 

And all comes down to the solidified relationship I have with them. I can trust my team to deliver when needed! 

So yes, schedule regular check-in calls with your clients. Use these calls to not only discuss project progress but also to understand their current challenges, celebrate their wins, and genuinely show interest in their business beyond the scope of your services. 

In the end, people buy from people.

Timing Your Upsell

Timing is everything when it comes to upselling—knowing when your client is most receptive can make all the difference.

Knowing the best moment to present an upsell is more art than science. You need to understand 2 things beforehand:

1. Your client's business cycle.
2. Their current level of satisfaction with your services.

Think about it - if your client hasn’t achieved growth with your work, and isn’t satisfied with your delivery and strategy, why would they pay you more?

That said, if you time an upsell when a client is already considering an expansion, you can significantly increase your chances of success. 

On the other hand, a premature upsell can feel pushy and damage the client relationship.

In the end that’s what you need to gauge: timing.

To get the timing right, stay attuned to signals of growth, new challenges, or particularly high satisfaction with a recent deliverable. 

If a client is enthusiastic about the results of a marketing campaign you executed, it might be the perfect time to suggest enhancing their strategy with additional services like SEO or content marketing.

Sensitivity to the right timing shows your attentiveness to the client's needs and positions your upsell as a natural next step in their growth journey, instead of a pushy sales pitch.

Try it.

And that’s all for today!

To wrap up all that we discussed:

• More focus on client acquisition than on retention and upselling = High churn and lost opportunities.

• Shift from a service-focused to a business-growth approach

• Tailor your services to their goals to become an invaluable business partner.

• Continuously drive value to your client's business. 

• Upskill in complementary fields and handle more areas to become indispensable.

• Differentiate yourself by building genuine, humane relationships. 

• Trust and loyalty come from personal connections beyond professional services.

• Upsell with perfect timing by understanding your client's business cycle and their satisfaction level with your services. 

• The right moment can significantly increase your chances of success.

• See your clients as partners to build a sustainable and growing business.

Till then, see you next week!

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