‘I Want to Help … but Should I?’ 

Most leaders have been there: We see someone who needs help, and we quickly provide it, only to end up feeling taken advantage of. Maybe you helped an employee out of a financial jam, only to see them keep making bad decisions. Or you spent hours coaching a younger colleague and then watched him ignore your advice. Or you stepped in to “rescue” a teammate who wasn’t prepared and later realized that she now counts on you to save the day.

Especially in a time of so much need, almost everyone feels the pull of generosity. But at the same time, we can’t help but worry that our generosity isn’t really helping the person in the long run — or worse, that it will have negative consequences for us or the organization.

Not knowing how to balance these impulses can create inner turmoil. We want to help other people, but are stuck wondering, Does this person even deserve my help? or Am I being taken advantage of? or even Is giving this person a fish keeping them from learning to fish themselves?

These are very human feelings and valid concerns. And they pose a real dilemma for would-be givers and helpers. We shouldn’t let these concerns harden our hearts to generosity. But, on the other hand, constantly giving to people who are not maximizing their own time and resources might just be an invitation for them to squander ours. 

To navigate this, we need to embrace a mindset that I call “responsible generosity.” It requires us to examine our own motives and to really think about what the other person needs long-term. It is not a “get out of giving free” card; in fact, it may require us to give more of ourselves, which is so much harder but also more meaningful than writing a check.

Here are a few tips on practicing responsible generosity:

Take a hard look at why you’re giving. Are you a co-dependent giver? Do you help others because you have a deep need to feel good about yourself; to be loved and appreciated; or to be seen as the smarter, stronger or more capable person? Are you doing it as a manipulation technique to get the other person to do something for you in return? Your focus should be on how the gift will impact the other person’s life, not on what you’re getting out of it.

For example, while we’d all like for our generosity to be met with gratitude, do you find yourself thinking, Is this person acting grateful enough? This only sets us up for resentment when people don’t react the way we think they should. Or, have you started thinking of yourself a “savior” whose role is to swoop in and save the day? 

Keep your ego out of the equation and stop worrying about whether the other person “deserves” it. Very few of us, if any, deserve the grace and good fortunate that comes our way. Try to stay focused on the other person’s needs and how you can truly help them.

Make sure that by helping others in the short-term, you aren’t setting them up for long-term failure. When we are constantly saving others from the natural consequences of their actions, we rob them of an opportunity to experience accountability. Because they’re not motivated to do better, they don’t improve and grow. By perpetually “helping” them, we keep them from ever becoming self-reliant. Sometimes the most loving thing to do is to say no.

If your teammate has a pattern of coming to meetings unprepared, and you consistently pick up her slack, what you’re teaching her is that you’ll always be there to cover for her. This sets up a dangerous long-term pattern of reliance and makes it harder for her to learn responsibility. Better to let her experience the natural consequences of not doing the work. Constantly saving the day might feel good to you, but it’s not helping her in the long run.   

Think beyond financial giving. Sharing your time and wisdom may be a more powerful form of generosity. There are many times when simply writing a check is not the best way to be generous. Instead, we should think critically about how to be generous with all our resources, including time and wisdom/knowledge. If you know someone who is constantly in need of financial rescuing, the best way to help might be to guide them to a better way of living.

If an employee, co-worker or friend is frequently in trouble, we may have the time or money to offer immediate assistance, but guidance, coaching and accountability are often more valuable. You might offer to help with budgeting or time management, for example. Just be sure not to do it in a judgmental way; always come from a place of love. You might even ask them if they’d like you to be their accountability partner in the future to help them stay on track. 

Consider setting reasonable conditions on gifts. If it’s clear to you that a person is trapped in a self-destructive pattern, you can often help them break out of it by asking them to make small, incremental behavior changes in exchange for your assistance. Tell them up front that if they don’t follow through, there will be no more help. Just be sure to use this tough love not as a club or punishment but as a motivation to change. Helping people “win” by taking steps to improve their life is good for them and good for you, too.

I once had a friend who would frequently get into financial jams and ask for a “loan,” which never got paid back. He was constantly job-hopping for an extra 50 cents an hour. Those jobs often looked better to him but turned out to be temporary; he would get laid off and come back asking for more. Finally, after yet another request, I agreed to help if he would agree to stay at his current job for a full year, regardless of how much more he could make elsewhere. He stuck to this agreement and learned the value of steady income that he could depend on.

Don’t try to go at it alone. Connect with networks that can amplify the impact of your generosity. Giving money directly to people who need it is not always the best way to help. A classic example is when someone struggling with addiction uses a donation to buy drugs rather than food — perpetuating the destructive cycle they’re trapped in. Community networks are designed to help people through tough times. If you feel called to give but lack the time/energy to make sure your gift is used responsibly, find a partner in your community who can. 

In most communities, there are amazing groups like churches, nonprofits and charity groups that stay hyper-focused on improving people’s lives long-term. Supporting their work and then helping connect them with those in need, might be the best way to help.  

Before giving money, our church gets to know the family, their needs and what is causing the issue — and then gives strategically to help people address the root cause.

Think about it this way: None of us have unlimited money, time or energy. That’s true of individuals, and it’s true of companies. We must be good stewards of our resources or they will quickly be depleted.

The more responsible we are with our giving, the more we can give. It’s that simple. And giving, when it’s done with the right spirit, feels great to everyone involved.

Gary Harpst is the author of Built to Beat Chaos: Biblical Wisdom for Leading Yourself and Others. He is the founder and CEO of LeadFirst. LeadFirst was founded in 2000 (as Six Disciplines) with a mission of building effective leaders and helping small and mid-sized companies manage change, grow and execute. Its four-part leadership development system — comprised of people skills, data-driven management skills, management platform and just-in-time learning — helps organizations bring order out of this swirling chaos.

Having been a CEO for 40 years, Harpst has experienced the challenges of every aspect of business ownership, from startup to rapid growth to acquiring other companies to being acquired. (Solomon Software, which he co-founded, was purchased by Great Plains and ultimately sold to Microsoft.) He is a keynote speaker, writer, and teacher whose areas of focus include leadership, business and the integration of faith at work. His passion is speaking about what effective leaders need to know, do and be to overcome the chaos of everyday life. He has been recognized as one of the Top 100 of the nation’s top thought–leaders in management and leadership by Leadership Excellence magazine. In addition to Built to Beat Chaos, he has written two other books: Six Disciplines for Excellence and Execution Revolution.

Built to Beat Chaos: Biblical Wisdom for Leading Yourself and Others (Wiley, April 2023, ISBN: 978-1-3941584-0-9, $25.00) is available at bookstores nationwide, www.wiley.com, and from major online booksellers.

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