Questions to ask
Technology
Core Advisor Workstation
The advisor workstation is the daily operating system of the practice. Advisors should understand whether it saves time or creates friction.
- What daily tasks can I complete inside the core workstation without jumping between multiple systems?
- Does the workstation combine CRM, account opening, trading, reporting, billing, service requests, and client data in one place?
- How many separate logins, systems, or vendor tools will my team need to use each day?
- Can the platform support my current team structure, workflows, client segmentation, and service model?
- How much training will my team need before the system becomes efficient after transition?
Account Opening & Onboarding
Account opening can make or break the client transition experience. Advisors should test how cleanly paperwork, transfers, and signatures are handled.
- Can new accounts be opened digitally with prefilled data, e-signature, and minimal manual paperwork?
- How does the platform handle ACATs, direct transfers, retirement accounts, annuities, alternatives, and complex household relationships?
- What tools exist to track account status, missing items, rejected paperwork, and NIGO issues?
- How much of the client onboarding process can my staff manage without calling the home office?
- What does the client experience look like from the moment they agree to transition through the account opening process?
Trading & Portfolio Management
Trading technology should match how the advisor actually manages portfolios, whether they use models, SMAs, fixed income, alternatives, or custom portfolios.
- Does the platform support my preferred investment process, including models, custom portfolios, block trading, rebalancing, and tax management?
- Can I trade efficiently across households, accounts, strategies, and sleeves without excessive manual work?
- What rebalancing, drift monitoring, tax-loss harvesting, and proposal tools are available?
- How does the platform support fixed income, alternatives, SMAs, direct indexing, annuities, and other product types I currently use?
- Will I control portfolio construction, outsource implementation, or have access to both options?
CRM & Workflow Automation
The CRM should help the practice run cleaner, not become a glorified contact database. Advisors should evaluate automation and team accountability.
- Does the CRM support my client segmentation, service calendar, review meeting cadence, and household tracking?
- Can my team create workflows for onboarding, service requests, client reviews, money movement, beneficiary updates, and follow-ups?
- Are reminders, tasks, notes, emails, and activity history easy to track across the team?
- Can the CRM support prospect pipeline management, campaigns, referrals, and business development activity?
- How much customization is available without needing a third-party consultant or major setup project?
Financial Planning Tools
Planning technology matters because it shapes the client conversation. Advisors should evaluate both advisor-side functionality and client-facing experience.
- Which financial planning tools are available, and are they included or paid for separately?
- Can the planning software support retirement income, tax planning, estate planning, insurance, education, cash flow, and scenario modeling?
- Does the tool integrate with client accounts, held-away assets, CRM data, proposals, and reporting?
- Is the client-facing planning experience simple enough for clients to understand and actually use?
- Can I use my preferred third-party planning software if I do not want to use the firm’s default tool?
Integrations
Disconnected systems create hidden time costs. Advisors should evaluate whether the technology stack works together or creates duplicate work.
- Which systems integrate natively, and which require manual entry, exports, uploads, or third-party workarounds?
- Does the platform offer single sign-on across the tools my team will use every day?
- How clean are the data feeds between CRM, planning, reporting, billing, trading, custodian, and client portal systems?
- Can I continue using my preferred third-party tools, or will I be forced into the firm’s default technology stack?
- Who is responsible for integration setup, troubleshooting, data migration, and ongoing maintenance?
Client Portal
The client portal becomes part of the client experience immediately after transition. Advisors should understand what clients will see and use.
- What can clients access through the portal, including balances, performance, statements, documents, tax forms, planning tools, and secure messages?
- Is the portal easy enough for older, less tech-savvy, or high-net-worth clients to use without frustration?
- Can clients view held-away assets, household-level reporting, goals, planning progress, and advisor-shared documents?
- How does the portal compare to what my clients currently use at my existing firm?
- What client education, onboarding support, or troubleshooting resources are available during the transition?
Mobile App
A weak mobile app can create unnecessary client complaints. Advisors should evaluate mobile usability before moving clients over.
- What can clients do in the mobile app versus the desktop portal?
- Is mobile login simple, secure, and reliable for clients who primarily use their phone?
- Can clients view account values, performance, statements, documents, messages, and planning information from the app?
- How highly adopted is the mobile app among clients, and what common complaints do advisors hear?
- Will the mobile experience feel like an upgrade or downgrade compared to what my clients currently have?
Reporting & Billing
Reporting and billing affect both client trust and advisor cash flow. Advisors should test flexibility, accuracy, and client readability.
- Can reports be customized by household, account, objective, model, sleeve, benchmark, time period, and client preference?
- Does the reporting system support performance, allocation, transactions, income, realized gains/losses, and household-level summaries?
- How flexible is the advisory billing system for different fee schedules, breakpoints, householding, discounts, and billing methods?
- Are reports and fee calculations easy for clients to understand and easy for my team to audit?
- How are billing errors, fee changes, refunds, closed accounts, and partial-period billing handled?
Tech Support & Training
Even good technology fails if the advisor and staff cannot learn it quickly. Support and training are critical during the first 90 days.
- What live training is provided before, during, and after the transition?
- Will my team have dedicated technology support, or will we rely on a general help desk?
- How quickly are common issues resolved during the transition period?
- Are there role-specific training paths for advisors, operations staff, assistants, traders, and client service team members?
- What ongoing resources exist after the initial transition, including webinars, knowledge bases, live support, and adoption coaching?
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