How to navigate a tricky boss + manage upwards
In this Q&A with Kate Waterfall Hill we explored how to work with a challenging boss and manage upwards.
Kate isn’t your typical leadership coach. While she holds the expected credentials (ICF and ILM qualifications) and brings over 30 years of business experience, she’s mastered the rare art of blending sharp leadership acumen with engaging humour. The result is transformative coaching that’s as insightful as it is enjoyable.
Her journey began at a mid-sized marketing agency, where she rapidly rose to become Managing Director at just 29. There, she led major accounts including Virgin and Vodafone, steering the agency through venture capital investment, an acquisition, and a management buyout.
In 2007, Kate established her own consultancy, advising CEO founders and SMEs before finding her true calling in executive coaching. She’s now best known for her viral character “Linda, the bad manager” – an alter ego whose leadership mishaps have amassed over 100 million views and 200,000+ social media followers.
Kate answered these Qs in this order:
- ZARA asked: My manager is under a lot of pressure but when asking for clarification on tasks, because communication is not always clear, the response is sometimes sarcastic and regularly irritated. Any tips on how to navigate this? I find it wearing.
- PRIYA asked: My line manager doesn’t have any time for me. 1:1s keep getting cancelled, she doesn’t reply to my emails… I know she’s busy but I feel quite alone. Any tips for how I can get the support I need?
- SARAH asked: I have 2 children under 5. My manager has children who are now grown up and although she says she understands, it really doesn’t feel like she does. She sets me unrealistic deadlines when she knows I have to do nursery pick up, contacts me on my day off, and doesn’t seem to get it if I’m ever late in after drop off. I’m trying really hard to keep up but I’m worried I’m just going to burn out. What would you suggest?
- ANONYMOUS: I have a colleague who is hostile to me (undermines me and my old manager used to take small steps to help. My new manager refuses to acknowledge there is a problem. How do I deal with this?
- ANONYMOUS asked: How to deal with a new boss who got the job you both applied for and is talking performance management and accountability when previously the feedback I’ve received previously was to deliver through others. Do I need to leave or work this through with her? How do I convey my competence?
- FRANCESCA asked: I recently had a feedback session with my manager and he mentioned some negative feedback that I really didn’t agree with. I tried to explain this but he didn’t listen and I even came out wondering if he was right and I was wrong! It’s not a once-off sadly… Any advice on how to manage this?
- CHRYSTAL asked: If a boss is often cold or impersonal, any tips to help improve relationship?
Kate’s CRYSTAL CLEAR model
In answer to Zara’s question, Kate shared a model for getting clarity on what is required on a substantial project:
CRYSTAL CLEAR
Context:
– Why is this task necessary?
– How does it align with team/company goals?
– What’s the background/history we should know?
Requirements:
– Who is the end user/audience?
– What specific deliverables are needed?
– What does “good” look like?
Yield:
– What impact/outcome are we aiming for?
– How will success be measured?
– What’s the business value?
Scope:
– What’s in and what’s out?
– Are there any constraints/limitations?
– What assumptions should we challenge?
Timeline:
– When is it needed by?
– Are there interim milestones?
– How does this fit with other priorities?
Authority:
– Who can make decisions?
– Who needs to be consulted?
– Who should be kept informed?
Links:
– Which other projects/teams does this connect to?
– What existing work can we leverage?
– Where can I find relevant resources/examples?
Concerns:
– What are the key risks/challenges?
– What has been tried before?
– Where might we need extra support?
Learning:
– What similar projects can we learn from?
– Who has expertise we can tap into?
– What should we watch out for?
Expert tip: Frame these questions as helping you deliver better results, not criticising the brief. “To make sure I nail this, could you help me understand…”
You rarely need to ask ALL of these – pick the most relevant based on the task and your boss’s style. But having this mental checklist helps ensure you don’t miss crucial information.
