Learn the do’s and don’ts of helping someone navigate grief, illness, loss, and challenging seasons with practical advice from business owners who’ve been there.
When someone you care about faces a difficult time; whether it’s grief, chronic illness, depression, loss, or burnout, knowing how to help can feel overwhelming. You want to be supportive, but fear saying the wrong thing or making matters worse.
As business leaders and entrepreneurs, we often encounter colleagues, clients, and team members going through challenging seasons. The way we show up during these moments doesn’t just impact our personal relationships; it shapes our professional reputation and builds lasting loyalty.
The Challenge of Knowing How to Help
Many well-intentioned people freeze up when someone they know is struggling. The uncertainty about what to say or do often leads to doing nothing at all; which can feel like abandonment to the person who’s suffering.
After experiencing challenging times firsthand, including a cancer scare, personal injury attorney Brooke Boltz learned valuable lessons about what actually helps versus what can unintentionally hurt when someone is in a valley.
5 Effective Ways to Support Someone During Hard Times
1. Send Simple, Encouraging Text Messages
The most effective support often comes in the simplest form: a brief, encouraging text message.
Effective examples include:
- “I’m praying for you today”
- “Thinking of you right now”
- “You don’t need to respond; just wanted you to know I care”
Why this works:
- No pressure to respond with lengthy updates
- Shows they’re not forgotten
- Provides gentle presence without overwhelming them
- Can be sent consistently over time
The key is consistency. While many people reach out initially, fewer continue checking in weeks or months later when support is still desperately needed.
2. Share Encouraging Music and Voice Messages
Music ministers to the soul in ways words sometimes cannot.
Consider sending:
- Worship songs that have encouraged you
- Instrumental tracks that bring peace
- Voice memos with genuine, animated encouragement
- Collaborative playlists from groups or teams
Voice memos offer a perfect middle ground between impersonal texts and overwhelming phone calls. They allow the recipient to hear emotion and sincerity without feeling pressured to engage in lengthy conversations.
3. Give Practical, Comfort-Focused Gifts
The most appreciated gifts address real, practical needs rather than just looking good.
Comfort items that make a difference:
- Soft, fluffy blankets (perfect for recovery time)
- Support pillows or specialized pillows for medical needs
- Favorite chocolates or comfort foods
Practical services that provide relief:
- Uber Eats or meal delivery gift cards
- House cleaning services
- Errand running (grocery shopping, prescription pickup, school transportation)
Pro tip: Instead of asking “What can I do?” be specific: “I’m going to the grocery store… what do you need?” or “I’m picking up my kids at 3pm; I’ll grab yours too.”
4. Send Handwritten Cards and Notes
Sometimes the biggest gift is knowing someone thought of you without needing anything in return.
Effective approaches:
- Handwritten cards that don’t require responses
- Simple notes that say “just wanted you to know you’re loved”
- Bible verses or inspirational quotes
- “No need to respond” messages that remove pressure
5. Practice Long-Term, Low-Pressure Support
Grief and hardship don’t follow convenient timelines. The initial flood of support often fades just when it’s needed most.
Sustainable support strategies:
- Weekly or bi-weekly check-ins for months, not just weeks
- “Still thinking of you” messages that require no response
- Understanding that non-response doesn’t mean lack of appreciation
- Continuing to reach out even when others have moved on
What NOT to Do: Well-Meaning Mistakes
Avoid Rushing to Silver Linings
Common phrases that can hurt rather than help:
- “At least it hasn’t spread”
- “At least they’re in a better place now”
- “Look on the bright side”
- “Everything happens for a reason”
Why this backfires: When someone says “at least,” what the struggling person hears is “your pain isn’t valid.” They’re likely already aware of positive aspects but need space to process their grief or fear.
Better approach: Validate their feelings by saying “This is really hard. I’m here with you. You’ve got this.”
Don’t Disappear Because You Don’t Know What to Say
Your presence matters more than perfect words. Many people avoid reaching out because they fear saying the wrong thing. However, silence feels like abandonment.
Simple alternatives when you’re unsure:
- “I’m here and I care”
- “Thinking of you”
- Send a card or Bible verse
- Share that you’re praying for them
Ask Deeper Questions (With Close Relationships)
Instead of repeatedly asking “How are you doing?” which requires the same medical updates, consider asking:
- “Has God revealed anything new to you through this challenge?”
- “What learning experiences have surprised you during this time?”
- “How can I pray specifically for you today?”
Note: These deeper questions should only be asked by close friends or family members, with appropriate timing and sensitivity.
The Business Impact of Showing Up
In both personal and professional contexts, the people who show up during difficult times create lasting impressions. These relationships often translate into:
- Stronger client loyalty and referrals
- Deeper team bonds and employee retention
- Enhanced professional reputation
- Meaningful networking that goes beyond transactions
- Trust-based business relationships that weather challenges
The colleagues, clients, and business partners who provided consistent support during challenging times become the first people you think of for referrals, partnerships, and opportunities.
Key Takeaways for Supporting Others
Remember these principles:
- Consistency trumps perfection
- Simple gestures often have the greatest impact
- Practical help addresses real needs
- Long-term support matters more than grand gestures
- Your presence is more important than your words
- Avoid trying to fix or minimize their pain
The ultimate goal isn’t to eliminate someone’s suffering, but to ensure they don’t suffer alone.
Building Authentic Relationships Through Difficult Seasons
As entrepreneurs and business leaders, we have countless opportunities to show up authentically for others. When we support someone during their lowest moments, without agenda or expectation of return, we build something far more valuable than a business transaction. We build trust, loyalty, and meaningful relationships that can last a lifetime.
The truth is, we all face difficult seasons eventually. When we do, we remember not what people said, but who showed up. Be the friend, colleague, or business partner who sends the encouraging text, the soft blanket, the voice memo, or simply says “I see your pain and I’m not afraid to sit with you in it.”
People may forget what you said, but they’ll always remember how you made them feel… and that’s not just good friendship, it’s good business.
Looking for more insights on building meaningful business relationships and leading with purpose? Subscribe to the Ms. Biz podcast for weekly episodes on growing personally, professionally, and spiritually as an entrepreneur.