As business owners and directors, we all have them – those enormous tasks looming on the horizon that feel too daunting to even begin. They sit there, growing more intimidating by the day, while we busy ourselves with the comfort of day-to-day operations.
Business mentoring for leaders facing big decisions
These mammoth tasks often come with significant implications for our businesses. They’re the projects that keep us awake at night, yet somehow never make it to the top of our to-do list. Why? Because they’re complex, multifaceted, and often deeply personal.
Think about:
- Planning your exit from the business you’ve built
- Preparing for retirement
- Restructuring your organisation
- Developing succession planning
- Considering a merger or acquisition
- Expanding into new markets
- Addressing persistent profitability issues
- Resolving partnership disagreements
- Creating a comprehensive strategic plan
- Digitising or modernising outdated systems
These aren’t tasks you can simply delegate. They require your vision, your decision-making, and ultimately, your action.
The isolation of leadership
One of the most challenging aspects of being a business owner or director is the isolation. When facing significant business decisions, you might find yourself unable to discuss them openly with your team.
This isolation becomes particularly acute when:
- You’re considering selling the business but don’t want to create uncertainty
- You’re planning retirement but haven’t finalised the succession details
- You’re contemplating a restructure that might affect current positions
- You’re dealing with financial difficulties that would worry your staff
- You’re considering pivoting the business in a new direction
- You’re evaluating the performance of key team members
Having nobody to bounce ideas off, test your thinking, or simply share your concerns with can make these already daunting tasks feel impossible.
Enter the business mentor
This is precisely where a business mentor becomes invaluable. Not as someone to take over the task, but as someone who holds you accountable for tackling it yourself.
A mentor provides:
- Regular check-ins that create deadlines and momentum
- An experienced sounding board for testing ideas
- Challenge to your thinking when needed
- Objective perspective without internal company politics
- Confidentiality for sensitive topics
- Structure to break down mammoth tasks into manageable steps
Assessing your mentor’s credibility
When facing substantial business challenges, a mentor’s credibility isn’t about charisma or a winning personality—it’s about substantive experience that directly relates to your situation. Before committing to a mentoring relationship, thoroughly evaluate whether their background aligns with your specific needs.
The right mentor should demonstrate:
- Relevant commercial experience: Have they successfully handled situations similar to yours? Look for someone who’s actually been in the trenches, not just studied the theory.
- Breadth of business exposure: A mentor who has worked across different industries, company sizes, and business models brings valuable perspective to your specific challenge.
- Financial acumen: Can they understand and speak intelligently about your business numbers, cash flow considerations, and the financial implications of major decisions?
- Strategic thinking ability: Do they show capacity to see beyond immediate issues to longer-term implications?
- Practical problem-solving track record: Ask for specific examples of how they’ve helped others tackle similar mammoth tasks.
- Business network depth: Sometimes the value comes not just from their knowledge but from who they can connect you with when specialised expertise is needed.
- Demonstrable results: Can they point to concrete outcomes from their previous mentoring relationships or their own business experience?
- Industry recognition: How are they regarded by their peers? Look for evidence of respect within relevant business communities.
Remember, impressive qualifications and an engaging personality may make for pleasant conversations but won’t necessarily translate to effective guidance through difficult business challenges. What matters is their “business nous”—that practical wisdom that only comes from having personally experienced complex commercial situations including failures and setbacks.
The most valuable mentors often have the battle scars to prove they’ve faced significant business challenges themselves—both triumphs and disappointments. This real-world experience creates not just knowledge but intuition about what works, what doesn’t, and what pitfalls to avoid. Someone who has only experienced smooth sailing may lack the depth of insight that comes from weathering storms and making difficult recoveries.
The Accountability Factor
The magic of mentoring lies in accountability. When you know you’ll be meeting with your mentor in two weeks and they’ll ask about your progress, suddenly that mammoth task doesn’t seem quite so easy to avoid. But let’s be crystal clear: the work still sits with you. A mentor isn’t going to write your succession plan, negotiate your business sale, or restructure your organisation. They’re going to ask the right questions, provide guidance based on experience, and most importantly, ensure you keep moving forward.
Breaking down the mountain
Effective mentors help you slice that mammoth task into bite-sized pieces. Instead of staring up at an insurmountable mountain, you’re looking at a series of manageable steps.
For instance, if you’re tackling a significant business challenge, a mentor might structure accountability around:
- Review current situation with honest SWOT analysis
- Research industry standards and best practices
- Identify key stakeholders and their priorities
- Draft a phased implementation plan
- Establish clear metrics for measuring progress
- Create communication strategies for different audiences
- Review resource requirements and constraints
- Identify potential roadblocks and contingency plans
- Document critical processes and dependencies
- Address compliance and regulatory considerations
- Develop training needs for team members
- Set milestones with realistic timeframes
- Allocate responsibilities across the team
- Create feedback mechanisms to monitor progress
- Plan personal development needed to lead the initiative
- Schedule regular review points to adjust approach
Each check-in focuses on progress made and obstacles encountered, with adjustments to the plan as needed.
Being prepared to do the work
Having a mentor doesn’t make the work disappear – it makes the work happen. This requires commitment from you to:
- Be honest about progress (or lack thereof)
- Allocate dedicated time between sessions
- Come prepared to your mentoring meetings
- Be open to challenge and different perspectives
- Take action on agreed next steps
If you’re not prepared to put in this effort, mentoring won’t work. The accountability only functions when you’ve bought into the process.
The Confidential Space
Perhaps one of the most valuable aspects of mentoring is the confidential space it creates. When dealing with sensitive business matters, discretion is paramount.
A good mentor provides a secure environment where you can:
- Voice your real concerns about the business
- Express doubts about your own capabilities
- Explore options that might be controversial
- Discuss sensitive people issues
- Work through your fears about major changes
This confidential sounding board can be the difference between stagnation and progress when dealing with complex, sensitive business decisions.
The path to completion
The journey from daunting task to completed project isn’t always linear. There will be setbacks, new information, and adjustments along the way. A mentor helps you:
- Stay focused on the end goal
- Adapt to changing circumstances
- Celebrate progress milestones
- Learn from inevitable setbacks
- Maintain momentum through the entire process
Finding the right mentor
Not all mentors are created equal. When looking for someone to help you tackle your mammoth task, consider:
- Relevant experience in your industry or with your specific challenge
- A personality that complements yours – supportive yet challenging
- Clear expectations about the mentoring relationship
- Structured approach to accountability
- Chemistry that allows for honest, open dialogue
The right mentor becomes a trusted ally in your corner, genuinely invested in your success.
The reward of completion
There’s an immense satisfaction in finally ticking off that mammoth task that’s been hanging over you. Beyond the direct business benefits, you gain:
- Renewed confidence in your abilities
- Freedom from the mental burden of procrastination
- Valuable skills for tackling the next big challenge
- Pride in having done the difficult work
And often, the results are better than if you’d tackled it alone, thanks to the input, challenge and structure provided by your mentor.
The next challenge awaits
Business ownership is a continuous journey of challenges. Once one mammoth task is conquered, another will eventually take its place. Having established a productive mentoring relationship, you’ll have a proven approach for tackling whatever comes next.
Remember, the biggest tasks in business are rarely completed in isolation. Even the most capable, experienced business leaders benefit from structured accountability and a confidential sounding board.
So as you look at that daunting task you’ve been avoiding, consider this: it won’t complete itself, and going it alone makes it harder than it needs to be. A mentor won’t do the work for you, but they will ensure you do the work for yourself – and that makes all the difference.
If this blog has piqued your interest in working with me as your business mentor accountability partner, send me an email if you’d like to arrange an initial conversation, or fill out the contact form if you prefer.