The wrong questions lead to the wrong answers. Many companies only ask advisors superficial questions or are dazzled by polished presentations. The result: disappointments, budget overruns, failed projects. This article provides a thorough question catalogue that helps collect the right information before engagement and identify the suitable advisor.
Why the Right Questions Are Critical
Most companies ask the wrong questions:
- “Can you do this?” (Answer is always “Yes”)
- “How much does it cost?” (Without context, any price is meaningless)
- “When can you start?” (Availability says nothing about quality)
The right questions:
Are specific, not generic. Aim for substance, not claims. Demand evidence, not just promises. Uncover red flags before it’s too late.
A structured question catalogue helps collect relevant information quickly and make informed decisions.
Structure of the Question Catalog
Questions are organised into eight categories:
- Experience and Qualifications (Can they really do it?)
- Methodology and Approach (How do they work?)
- Team and Resources (Who does the work?)
- References and Track Record (Have they proven it?)
- Pricing and Budget (What does it really cost?)
- Deliverables and Results (What do we get?)
- Timeline and Availability (When will it be done?)
- Risks and Challenges (What can go wrong?)
For each category, you’ll find questions for initial conversations, in-depth questions for the shortlist, and critical questions that uncover red flags.
1. Experience and Qualifications
Questions for Initial Conversation
“How long have you been active in this field?” What you learn: Overall experience and market knowledge. Watch for: General professional experience is not the same as specific expertise. Someone with 20 years IT experience doesn’t automatically have 20 years cybersecurity expertise.
“What is your specialisation?” What you learn: Focus vs. generalist. Watch for: Vague answers like “We do everything” are a warning sign. Excellent service providers have clear focus areas.
“What qualifications and certificates do you have?” What you learn: Formal evidence of competence. Watch for: Industry-relevant certificates (e.g., FMH title, ISO 27001, CREST) are more important than generic management certificates.
“In which industries do you have experience?” What you learn: Industry knowledge and transferability. Watch for: Industry experience is especially important in regulated or highly specialised areas (e.g., pharma, fintech, public administration).
In-depth Questions for Shortlist
“How many comparable projects have you completed in the last two years?” What you learn: Currency of experience and frequency. Watch for: “Comparable” is key. Ask about projects with similar size, complexity, and objectives.
“What was your most complex project in this area?” What you learn: Maximum capacity and limits. Watch for: If your project is significantly more complex than anything the provider has done before, be cautious.
“What specific challenges do you know from our industry?” What you learn: Depth of industry knowledge. Watch for: Generic answers (“Every industry has its challenges”) show lacking knowledge. Expect specific examples.
“How do you stay current? What continuing education have you recently completed?” What you learn: Currency of knowledge and willingness to learn. Watch for: In dynamic fields (tech, law, medicine), regular continuing education is mandatory.
Critical Questions (Red Flag Detector)
“For what types of projects are you NOT suitable?” What you learn: Self-reflection and honesty. Watch for: Those who say “We can do everything” are either dishonest or unrealistic. Good providers know their limits.
“Which project went wrong for you and why?” What you learn: Error culture and learning ability. Watch for: Those who claim never to have made mistakes are lying. Important is what was learned from them.
“Can you provide evidence of your qualifications?” What you learn: Willingness to be transparent. Watch for: Those who refuse to submit certificates or evidence may have something to hide.
2. Methodology and Approach
Questions for Initial Conversation
“How do you typically proceed with such projects?” What you learn: Approach model and structure. Watch for: There should be a recognizable phase model (e.g., analysis, concept, implementation, completion).
“What methodology do you use?” What you learn: Theoretical foundation (e.g., Agile, PRINCE2, Design Thinking). Watch for: The methodology should fit the task. Agile is not the solution for everything.
“How do you involve the client in the process?” What you learn: Degree of collaboration and communication intensity. Watch for: Some projects require close collaboration, others don’t. Clarify what’s expected.
“How do you ensure quality?” What you learn: Internal QA processes. Watch for: Lacking quality assurance is a massive risk. Ask about concrete reviews or tests.
In-depth Questions for Shortlist
“Can you show me your typical project plan for such a project?” What you learn: Detail and realism of planning. Watch for: A good project plan shows phases, milestones, deliverables, and dependencies.
“How do you measure project success?” What you learn: Success definition and measurability. Watch for: Vague formulations like “client satisfaction” are insufficient. Expect concrete KPIs.
“How do you handle changes or scope expansions?” What you learn: Change management process. Watch for: Changes are inevitable in almost every project. There should be a clear process for handling them.
“What tools do you use for project management and communication?” What you learn: Professionalism and compatibility. Watch for: Tools should fit your IT environment or at least be compatible.
“How often and in what form do we receive status updates?” What you learn: Communication frequency and transparency. Watch for: Regular updates (e.g., weekly) are standard in complex projects.
Critical Questions (Red Flag Detector)
“What happens if a milestone is not achieved?” What you learn: Handling of delays and responsibility. Watch for: Those who only cite external factors as causes (“The client didn’t deliver”) take no responsibility.
“How do you handle disagreements between your team and ours?” What you learn: Conflict ability and solution orientation. Watch for: Lacking conflict resolution mechanisms lead to escalating situations.
“What is your plan B if your main approach doesn’t work?” What you learn: Flexibility and problem-solving competence. Watch for: Rigid adherence to one approach without alternatives is risky.
3. Team and Resources
Questions for Initial Conversation
“Who specifically will work on our project?” What you learn: Actual project members vs. salesperson. Watch for: The eloquent salesperson is often not the one who later does the work.
“What experience do the specific project members have?” What you learn: Seniority and competence of actual team. Watch for: Junior staff under senior guidance can work, but it should be transparent.
“How large is your team?” What you learn: Capacity and resource availability. Watch for: Too small teams can become bottlenecks in case of illness or overload.
“Do you work with freelancers or subcontractors?” What you learn: Team structure and control. Watch for: Freelancers are not problematic per se, but you should know who actually works and who’s liable.
In-depth Questions for Shortlist
“Can I meet the project members in advance?” What you learn: Transparency and opportunity for assessment. Watch for: Those who refuse to introduce the team may have something to hide.
“How are roles distributed in the project team?” What you learn: Responsibilities and clarity. Watch for: It should be clear who’s responsible for what (e.g., project management, technical implementation, quality assurance).
“What happens if a team member drops out (illness, termination)?” What you learn: Backup resources and risk management. Watch for: In smaller teams, this risk is higher. There should be a plan.
“What percentage of your capacity will our project require?” What you learn: Prioritization and availability. Watch for: If your project only accounts for 10% of capacity, prioritisation could be problematic.
“Who is our main contact person and how available is he/she?” What you learn: Communication channels and availability. Watch for: Frequently changing contact persons or hard-to-reach people are frustrating.
Critical Questions (Red Flag Detector)
“Will the people I’m meeting now actually work on the project?” What you learn: Honesty vs. “bait and switch.” Watch for: It’s a classic trick to show experienced people in the pitch and then deploy juniors.
“How many other projects are team members handling in parallel?” What you learn: Availability and focus. Watch for: Too many parallel projects lead to bottlenecks and quality loss.
“Do you have capacity for our project or do you first need to hire people?” What you learn: Current utilisation and risk. Watch for: If people must first be recruited, the start is delayed and quality is uncertain.
4. References and Track Record
Questions for Initial Conversation
“Can you name three current references I may contact?” What you learn: Willingness to be transparent and availability of references. Watch for: Those who refuse to name references may not have good ones.
“Which reference projects are comparable to ours?” What you learn: Relevance of experience. Watch for: Comparability is crucial. An app project is not comparable to an enterprise website.
“How long do you typically work with your clients?” What you learn: Client retention and satisfaction. Watch for: Long-term client relationships are a strong indicator of quality.
“Do you have follow-up orders from existing clients?” What you learn: Client satisfaction and trust. Watch for: Clients who return are satisfied. One-time projects can be a warning signal.
In-depth Questions for Shortlist
“What do your clients say about working with you?” What you learn: Self-image vs. external image. Watch for: Compare these statements with what reference clients actually say.
“Which client was most difficult and why?” What you learn: Handling of challenges and conflict ability. Watch for: Those who only assign external blame (“The client was impossible”) don’t reflect.
“Are there projects you’re particularly proud of? Why?” What you learn: Values and priorities of the provider. Watch for: Those who only rave about big names or high budgets may prioritise prestige over quality.
“What awards or industry recognition have you received?” What you learn: External validation of quality. Watch for: Genuine industry awards (e.g., from associations) are valuable, purchased “awards” are not.
Critical Questions (Red Flag Detector)
“May I contact reference clients directly or only through you?” What you learn: Control over reference communication. Watch for: If only pre-filtered or “accompanied” conversations are possible, be cautious.
“Why did your last client drop out?” What you learn: Handling of failed relationships. Watch for: Nobody has a 100% success rate. Important is what was learned from mistakes.
“Are there references you would NOT name? Why?” What you learn: Honesty about problematic projects. Watch for: This question is uncomfortable, but the answer is very revealing.
5. Pricing and Budget
Questions for Initial Conversation
“How do you calculate your prices? (Fixed price, time & materials, hybrid model)” What you learn: Price model and flexibility. Watch for: Fixed price gives security but little flexibility. Time & materials is flexible but budgetarily riskier.
“What is included in your offer, what is not?” What you learn: Scope of services and hidden costs. Watch for: Travel costs, licences, infrastructure are often not included and can be significant.
“How do you handle scope changes and how are they billed?” What you learn: Change management and cost risks. Watch for: There should be a clear process for how changes are treated and priced.
“What are your payment terms?” What you learn: Payment modalities and cash flow. Watch for: High advance payments (>30%) are unusual and risky. Milestone-based payments are fair.
In-depth Questions for Shortlist
“Can you break down your cost calculation in detail?” What you learn: Transparency and traceability. Watch for: A detailed breakdown shows what you’re paying for (hours, roles, materials).
“What happens if the project takes longer than planned?” What you learn: Risk sharing and responsibility. Watch for: With fixed price, the provider bears the risk. With time & materials, you bear it. This should be fairly distributed.
“Are there guarantees or warranties?” What you learn: Post-contractual protection. Watch for: Serious providers offer warranties (e.g., 6-12 months defect correction).
“How do your prices compare to the market?” What you learn: Market positioning (premium, mid-range, budget). Watch for: Extremely low prices are often a warning sign. Quality has its price.
“What payment milestones do you suggest?” What you learn: Risk sharing and fairness. Watch for: Fair milestones are tied to service delivery (e.g., 30% at start, 40% after concept, 30% after completion).
Critical Questions (Red Flag Detector)
“What happens if we need to terminate the project prematurely?” What you learn: Exit clauses and fairness. Watch for: One-sided clauses (you pay everything but get nothing) are unfair.
“What costs come on top of the offer?” What you learn: Hidden costs and transparency. Watch for: Serious providers proactively point out possible additional costs.
“Why is your price significantly lower/higher than other providers?” What you learn: Price justification and plausibility. Watch for: Extreme deviations should be justifiable. Otherwise, either service or realism is missing.
6. Deliverables and Results
Questions for Initial Conversation
“What exactly are the results (deliverables) of this project?” What you learn: Concrete services and measurability. Watch for: Vague formulations (“consulting”, “support”) are problematic. Expect concrete outputs.
“In what form will the results be delivered?” What you learn: Format and usability. Watch for: Digital vs. physical deliverables, editable formats vs. PDFs, documentation vs. only verbal handover.
“Who owns the rights to the results?” What you learn: Ownership and usage rights. Watch for: For most projects, you should receive all rights. If not, clarify exactly what you may and may not do.
“How do you ensure the results meet our requirements?” What you learn: Quality assurance and acceptance. Watch for: There should be a structured acceptance process with clear criteria.
In-depth Questions for Shortlist
“Can you show me examples of typical deliverables?” What you learn: Quality and detail of results. Watch for: Examples give a good impression of actual quality (NDA-cleaned).
“How thorough is the documentation?” What you learn: Traceability and knowledge transfer. Watch for: Good documentation enables you to continue working independently after project completion.
“What happens if we’re dissatisfied with a deliverable?” What you learn: Iteration process and goodwill. Watch for: There should be room for feedback and adjustments without immediately incurring additional costs.
“How is the handover of results conducted?” What you learn: Handover process and knowledge transfer. Watch for: A structured handover with training/briefing is often important, especially in complex projects.
“Are there trainings or workshops for our team?” What you learn: Enablement to use the results. Watch for: For tools, processes, or methods, training is often crucial for success.
Critical Questions (Red Flag Detector)
“What happens if the results don’t work or are defective?” What you learn: Liability and rectification. Watch for: Serious providers stand by their results and fix defects free of charge afterward.
“Are the deliverables final or only drafts?” What you learn: Degree of completion and follow-up work. Watch for: If only drafts are delivered, you must do follow-up work yourself or pay additionally.
“Can we further develop the deliverables ourselves after project completion or are we dependent on you?” What you learn: Dependency vs. autonomy. Watch for: Vendor lock-in is problematic. You should be independent after project completion.
7. Timeline and Availability
Questions for Initial Conversation
“When can you start?” What you learn: Availability and utilisation. Watch for: Immediate availability can mean the provider is not fully utilised (warning sign).
“How long does such a project typically take?” What you learn: Realism and experience values. Watch for: Compare the time estimate with other providers. Extreme deviations are suspicious.
“What are the biggest time risks in this project?” What you learn: Risk awareness and realism. Watch for: Those who see no risks plan unrealistically.
“How flexible are you with schedule changes?” What you learn: Adaptability and goodwill. Watch for: Rigid schedule requirements can be problematic if something shifts on your side.
In-depth Questions for Shortlist
“Can you provide a detailed timeline?” What you learn: Planning quality and realism. Watch for: A good timeline shows phases, milestones, dependencies, and buffers.
“What preliminary work do you need from us and by when?” What you learn: Dependencies and own responsibilities. Watch for: Clarify early what you must deliver, otherwise it becomes a delay cause.
“How much time must we invest ourselves?” What you learn: Own effort and resource commitment. Watch for: Some projects require intensive participation, others less. This should be transparent.
“What happens if you cannot meet the schedule?” What you learn: Consequences and contractual penalties. Watch for: For time-critical projects, delays should have consequences.
“Are there dependencies on other projects or providers?” What you learn: External risks and coordination needs. Watch for: Dependencies increase complexity and delay risk.
Critical Questions (Red Flag Detector)
“Why can you deliver so quickly?” What you learn: Plausibility of unrealistically short timelines. Watch for: If it sounds too good to be true, it probably is.
“What happens if we cause delays?” What you learn: Flexibility and goodwill with client delays. Watch for: Rigid contractual penalties even for delays on your side are unfair.
“Do you have other large projects running in parallel?” What you learn: Prioritization and capacity. Watch for: Too many parallel large projects can lead to bottlenecks.
8. Risks and Challenges
Questions for Initial Conversation
“What are the biggest risks in this project?” What you learn: Risk awareness and honesty. Watch for: Those who see no risks are either inexperienced or dishonest.
“What could go wrong?” What you learn: Realism and preparation. Watch for: Good providers have thought through risk scenarios and prepared countermeasures.
“How do you handle unexpected problems?” What you learn: Problem-solving competence and flexibility. Watch for: Processes for escalation and problem-solving should be defined.
“What dependencies exist that are outside your control?” What you learn: External risk factors. Watch for: Third-party providers, regulatory changes, or technical dependencies are often critical.
In-depth Questions for Shortlist
“What is your plan B if the main approach doesn’t work?” What you learn: Backup strategies and flexibility. Watch for: Rigid adherence to one approach without alternative is risky.
“How do you distribute risks between us and you?” What you learn: Risk allocation and fairness. Watch for: Fair contracts distribute risks according to influence possibilities. Whoever can control the risk should bear it.
“What are typical stumbling blocks in such projects and how do you avoid them?” What you learn: Experience and prevention. Watch for: Providers who have learned from mistakes proactively avoid typical problems.
“What insurance do you have (professional liability, business liability)?” What you learn: Protection in case of damages. Watch for: Serious providers have appropriate insurance, especially in risk-prone areas.
Critical Questions (Red Flag Detector)
“What was your biggest mistake in a similar project and what did you learn from it?” What you learn: Error culture and learning ability. Watch for: Those who admit no mistakes don’t reflect and will repeat them.
“What happens if you cannot successfully complete the project?” What you learn: Exit strategy and liability. Watch for: There should be clear regulations for what happens in case of failure (refund, damages, handover).
“Were there projects you had to decline? Why?” What you learn: Self-knowledge and limits. Watch for: Those who never decline projects may also take on unsuitable assignments.
Swiss Specifics: Questions About Local Context
Regulatory and Legal Aspects
“Are you familiar with relevant Swiss regulations (e.g., Data Protection Act, Banking Act, Medical Professions Act)?” What you learn: Local knowledge and compliance security. Watch for: In regulated industries, Swiss legal knowledge is crucial.
“Where is data stored and processed?” What you learn: Data protection and compliance (GDPR, FADP). Watch for: For some industries, data storage in Switzerland or EU is mandatory.
“Do you have experience with Swiss authorities (e.g., FINMA, FOPH, SECO)?” What you learn: Knowledge of regulatory processes. Watch for: Authority communication is often crucial in regulated projects.
Cultural and Linguistic Aspects
“In which languages can you work (German, French, Italian, English)?” What you learn: Language competence and communication ability. Watch for: In multilingual projects or cantons, this is crucial.
“Do you understand Swiss business culture (consensus orientation, federalism, directness)?” What you learn: Cultural sensitivity. Watch for: International providers often struggle with Swiss peculiarities (e.g., slow decision-making).
“Do you have experience with SMEs or mainly with large corporations?” What you learn: Compatibility with your company size. Watch for: Methods for corporations don’t always work for SMEs (and vice versa).
Geographic and Operational Aspects
“How important is physical presence in your projects?” What you learn: Remote vs. on-site. Watch for: In Switzerland, physical presence is often valued higher than abroad.
“Are you willing to travel regularly to Switzerland or do you have locations here?” What you learn: Availability and costs. Watch for: Travel costs and time investment can be significant with foreign providers.
“Do you know the differences between German-speaking Switzerland, Romandy, and Ticino?” What you learn: Regional understanding. Watch for: Switzerland is not homogeneous. Regional differences are relevant (language, culture, markets).
How to Evaluate Answers
Watch for Warning Signs
Vague or evasive answers: “It depends,” “We’ll have to see,” “We do it situationally.”
Exaggerated promises: “Guaranteed,” “Always,” “Never a problem,” “100% success rate.”
Lacking examples: When concrete questions only receive abstract answers.
Defensive behaviour: Provider reacts irritably to critical questions.
Inconsistent statements: Contradictions between different conversations or people.
Positive Signals
Concrete, specific answers: With examples, numbers, verifiable facts.
Honest self-reflection: Limits are named, mistakes are admitted.
Proactive risk notices: Provider points out challenges without prompting.
Willingness to be transparent: Evidence is submitted, references are named, documents are shared.
Questions for understanding: Provider asks questions to better understand your situation.
Structuring the Question Process
Phase 1: Initial Conversation (30-45 minutes)
Focus: Check basic fit. Questions about experience, methodology, team, availability. Goal: Decision whether provider makes the shortlist.
Phase 2: In-depth Conversation (60-90 minutes)
Focus: Detailed examination of shortlist candidates. In-depth questions across all categories. Goal: Request proposal and check references.
Phase 3: Reference Conversations (20-30 minutes per reference)
Focus: Validation by third parties. Structured interviews with at least three reference clients. Goal: Comparison between self-presentation and external perception.
Phase 4: Final Clarification (30 minutes)
Focus: Clarify open questions, address last concerns. Critical questions about risks, contract terms, contingency plans. Goal: Create final decision basis.
Conclusion: Questions as Decision Basis
The quality of your questions determines the quality of your decision. A structured question catalogue helps collect relevant information quickly:
Preparation is crucial: Define in advance which questions are particularly important for your project.
Ask all providers the same questions: Only this creates comparability.
Listen to what is NOT said: Evasive answers or lacking examples are warning signs.
Verify statements through references: Self-presentation and reality can diverge.
Document answers: You’ll need the information later for the decision.
Trust red flags: Warning signs in the selection process are indicators of later problems.
Asking the right questions takes time, but this time is the best investment in project success. Because the most expensive decision is the wrong choice of advisor.
Transparency Note: This article was created with the support of AI technology (Claude, Anthropic) and editorially reviewed. The content is based on established best practices in advisor and service provider selection as well as specific characteristics of the Swiss market.